松岡 浩司(マツオカ コウジ)
研究機構 研究推進室室長
工学部 応用化学科

研究者情報

■ 学位
  • 修士(工学), 成蹊大学
  • 博士(理学), 北海道大学
■ 研究キーワード
  • 生理活性物質
  • 生体高分子
  • 糖鎖高分子
  • 糖鎖デンドリマー
  • 糖鎖クラスター
  • 高分子化学
  • 生化学
  • 合成化学
  • 有機化学
  • 複合糖質
■ 研究分野
  • ライフサイエンス, 生物有機化学
  • ナノテク・材料, 有機合成化学
  • ナノテク・材料, 高分子化学
  • ライフサイエンス, 薬系化学、創薬科学, 水溶性高分子、デンドリマー、ゲル
  • ナノテク・材料, ナノバイオサイエンス, 糖鎖材料、生体適合材料
■ 研究シーズ
  • ベロ毒素, カルボシランデンドリマー, グロボ3糖, 糖鎖ポリマー, カルボシランデンドリマーをコアとした大腸菌O157:H7が産生するベロ毒素中和剤の開発
  • インフルエンザウィルス, カルボシランデンドリマー, 阻害剤, 糖鎖ポリマー, カルボシランデンドリマーをコアとしたインフルエンザウィルス阻害剤の開発
  • シクロデキストリン, 不斉合成, メチル化, シクロデキストリンを基盤とした機能材料の開発
■ 研究グループ
  • 機能分子設計, 高分子化学
■ 経歴
  • 2011年04月 - 現在, 埼玉大学, 大学院 理工学研究科 物質科学部門, 教授
  • 2001年01月 - 2011年03月, 埼玉大学, 工学部 機能材料工学科, 准教授
  • 1995年09月 - 2000年12月, 埼玉大学, 工学部 機能材料工学科, 助手
  • 1995年04月 - 1995年08月, 理化学研究所, 有機合成化学研究室, 奨励研究員
■ 学歴
  • 1995年, 北海道大学, 理学研究科, 生物科学専攻, 日本国
  • 1995年, 日本国
  • 1992年, 成蹊大学, 工学研究科, 工業化学専攻, 日本国
  • 1992年, 日本国
  • 1990年, 成蹊大学, 工学部, 工業化学科, 日本国
  • 1990年, 日本国
■ 受賞
  • 2005年03月, 東京糖鎖研究会奨励賞
    日本国
  • 1999年, ポスター賞(日本糖質学会)
    日本国
  • 1996年, 井上研究奨励賞
    日本国

業績情報

■ 論文
  • Incomplete functionalization of glycodendrimers: Effects on binding affinity with wheat germ agglutinin               
    Takahiko Matsushita; Naomichi Toda; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    European Journal of Medicinal Chemistry Reports, 2025年08月, [査読有り], [最終著者]
    研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.ejmcr.2025.100266
    DOI ID:10.1016/j.ejmcr.2025.100266, ORCID:181842730
  • Synthesis of Water-Soluble Glycopolymers Bearing Porphyrin by Means of Glycopolymer Assembly and Physical Properties of Glycopolymers Including Ability for Singlet Oxygen Production
    Yuta Komano; Miho Suzuki; Takahiko Matsushita; Tetsuo Koyama; Yoshihiro Ishimaru; Ken Hatano; Koji Matsuoka
    Biomacromolecules, 2025年04月, [最終著者, 責任著者]
    American Chemical Society (ACS), 研究論文(学術雑誌)
    DOI:https://doi.org/10.1021/acs.biomac.5c00121
    DOI ID:10.1021/acs.biomac.5c00121, ISSN:1525-7797, eISSN:1526-4602
  • Interpenetrating Polymer Network Capturing FRET-Sensitive Polymers Available for an Enzyme Assay               
    Kota Miyairi; Hirokatsu Arai; Takahiko Matsushita; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    Biomacromolecules, 2024年08月, [査読有り], [最終著者, 責任著者]
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1021/acs.biomac.4c00622
    DOI ID:10.1021/acs.biomac.4c00622, ORCID:164775308
  • Use of an oxazolidinone derivative of a sialyl thioglycoside as a useful glycosyl donor for α-favorable glycosidation with simple alcohols               
    Jianhong Zhang; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano; Koji Matsuoka
    Tetrahedron Letters, 2024年08月, [査読有り], [最終著者, 責任著者]
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tetlet.2024.155189
    DOI ID:10.1016/j.tetlet.2024.155189, ORCID:163137912
  • Preparation of fluorogenic glycopolymers having mannose moieties that can be used for determining the affinity of lectins by means of intermolecular FRET               
    Kota Miyairi; Takahiko Matsushita; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    Journal of Molecular Structure, 2024年06月, [査読有り], [最終著者, 責任著者]
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.molstruc.2024.137896
    DOI ID:10.1016/j.molstruc.2024.137896, ORCID:154504798
  • pH-Dependent proteolytic activity of histidine-pendant polyacrylamides               
    Shinzo Omiya; Hinako Yamochi; Tetsuo Koyama; Ken Hatano; Koji Matsuoka; Takahiko Matsushita
    European Polymer Journal, 2024年04月, [査読有り]
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.eurpolymj.2024.112898
    DOI ID:10.1016/j.eurpolymj.2024.112898, ORCID:154927803
  • Preparation of a water-soluble polymer having pheophorbide a side chains using glycopolymer assembly               
    Koji Matsuoka; Jyuichi Nakada; Masataka Nakazato; Takahiko Matsushita; Tetsuo Koyama; Ken Hatano
    Tetrahedron Letters, 2024年03月, [査読有り], [筆頭著者, 責任著者]
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tetlet.2024.154963
    DOI ID:10.1016/j.tetlet.2024.154963, ORCID:153781772
  • Synthetic assembly of α-O-linked-type GlcNAc using polymer chemistry affords sugar clusters, which effectively bind to lectins               
    Jyuichi Nakada; Takahiko Matsushita; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    Bioorganic & Medicinal Chemistry Letters, 2024年02月, [査読有り], [最終著者, 責任著者]
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmcl.2024.129616
    DOI ID:10.1016/j.bmcl.2024.129616, ORCID:150401885
  • Preparation of N-Linked-Type GlcNAc Monomers for Glycopolymers and Binding Specificity for Lectin               
    Takahiko Matsushita; Momoka Nozaki; Mio Sunaga; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    ACS Omega, 2023年10月, [査読有り], [最終著者, 責任著者]
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1021/acsomega.3c05151
    DOI ID:10.1021/acsomega.3c05151, ORCID:143076579
  • Preparation of a Water-Soluble Glycopolymer Bearing Porphyrin Skeletons and Its Biological Properties               
    Yoshihiro Ishimaru; Tomohide Moteki; Miho Suzuki; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano; Koji Matsuoka
    ACS Omega, 2023年10月, [査読有り], [最終著者, 責任著者]
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1021/acsomega.3c05581
    DOI ID:10.1021/acsomega.3c05581, ORCID:143076577
  • Proteolytic polymer: polyacrylamides functionalized with amino acids cleave bovine and human serum albumins               
    Takahiko Matsushita; Hinako Yamochi; Shinzo Omiya; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    Bioorganic & Medicinal Chemistry, 巻:92, 開始ページ:117422, 終了ページ:117422, 2023年09月, [査読有り], [最終著者, 責任著者]
    Elsevier BV, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmc.2023.117422
    DOI ID:10.1016/j.bmc.2023.117422, ISSN:0968-0896
  • Synthetic assembly of a series of glycopolymers having sialyl α2-3 lactose moieties connected with longer spacer arms               
    Ryota Adachi; Takahiko Matsushita; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    Bioorganic & Medicinal Chemistry, 巻:81, 開始ページ:117209, 終了ページ:117209, 2023年03月, [査読有り], [最終著者, 責任著者]
    Elsevier {BV}, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmc.2023.117209
    DOI ID:10.1016/j.bmc.2023.117209, ISSN:0968-0896, ORCID:128587217
  • Use of a Longer Aglycon Moiety Bearing Sialyl α(2→3) Lactoside on the Glycopolymer for Lectin Evaluation
    Ryota Adachi; Takahiko Matsushita; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    Polymers, 巻:15, 号:4, 開始ページ:998, 2023年02月, [査読有り], [最終著者, 責任著者]
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.3390/polym15040998
    DOI ID:10.3390/polym15040998, ORCID:128991652
  • Dendritic maleimide-thiol adducts carrying pendant glycosides as high-affinity ligands               
    Takahiko Matsushita; Naomichi Toda; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    Bioorganic Chemistry, 巻:128, 開始ページ:106061, 終了ページ:106061, 2022年11月, [査読有り], [最終著者, 責任著者]
    Elsevier BV, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bioorg.2022.106061
    DOI ID:10.1016/j.bioorg.2022.106061, ISSN:0045-2068
  • Modification of Fab Fragments by Dibromopyridazinediones Carrying Mono- and Double-Biotin Functionalities
    Takahiko Matsushita; Naoto Maruyama; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    ACS Omega, 巻:7, 号:38, 開始ページ:34554, 終了ページ:34562, 2022年09月, [査読有り], [最終著者, 責任著者]
    American Chemical Society (ACS), 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1021/acsomega.2c04379
    DOI ID:10.1021/acsomega.2c04379, ISSN:2470-1343, eISSN:2470-1343
  • Chemical modification of CNN 1. Complete protection of CNN
    Matsuoka, K.; Endo, D.; Adachi, R.; Koyama, T.; Matsushita, T.; Hatano, K.
    Tetrahedron Letters, 巻:103, 開始ページ:153986, 終了ページ:153986, 2022年08月, [査読有り], [筆頭著者, 責任著者]
    Elsevier {BV}, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tetlet.2022.153986
    DOI ID:10.1016/j.tetlet.2022.153986, ISSN:1873-3581, ORCID:122074667, SCOPUS ID:85133769537
  • Systematic synthesis of a series of glycopolymers having N-acetyl-D-glucosamine moieties that can be used for evaluations of lectin—carbohydrate interactions               
    Koji Matsuoka; Masaki Nakagawa; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano
    European Polymer Journal, 巻:168, 開始ページ:111101, 終了ページ:111101, 2022年04月, [査読有り], [筆頭著者, 責任著者]
    Elsevier BV, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.eurpolymj.2022.111101
    DOI ID:10.1016/j.eurpolymj.2022.111101, ISSN:0014-3057
  • Tough polymer with a gradual spatial change in the hydrogen bond density controlled by simple one-pot copolymerization               
    Shogo Ishizaka; Shintaro Nakagawa; Koji Matsuoka; Naoko Yoshie
    Polymer, 巻:246, 開始ページ:124748, 終了ページ:124748, 2022年04月, [査読有り]
    Elsevier BV, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.polymer.2022.124748
    DOI ID:10.1016/j.polymer.2022.124748, ISSN:0032-3861
  • Preparation of glycopolymers having sialyl α2 → 3 lactose moieties as the potent inhibitors for mumps virus               
    Koji Matsuoka; Takayuki Kaneshima; Ryota Adachi; Jiei Sasaki; Takao Hashiguchi; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano
    Bioorganic & Medicinal Chemistry Letters, 巻:52, 開始ページ:128389, 終了ページ:128389, 2021年11月, [査読有り], [筆頭著者, 責任著者]
    Elsevier BV, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmcl.2021.128389
    DOI ID:10.1016/j.bmcl.2021.128389, ISSN:0960-894X
  • Preparation of lauryl thioglycoside of N-glycolylneuraminic acid (Neu5Gc) as a useful glycosyl donor for assembly of an oligosaccharide containing Neu5Gc               
    Jianhong Zhang; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano; Koji Matsuoka
    Tetrahedron Letters, 巻:83, 開始ページ:153403, 終了ページ:153403, 2021年10月, [査読有り], [最終著者, 責任著者]
    Elsevier BV, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tetlet.2021.153403
    DOI ID:10.1016/j.tetlet.2021.153403, ISSN:0040-4039
  • Synthetic assembly of two β-cyclodextrins through a trehalose moiety as a linker1
    Ishimaru, Y.; Saito, Y.; Shiraishi, Y.S.; Esumi, Y.; Terunuma, D.; Kuzuhara, H.; Matsuoka, K.
    Tetrahedron Letters, 巻:78, 2021年, [査読有り], [最終著者, 責任著者]
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tetlet.2021.153287
    DOI ID:10.1016/j.tetlet.2021.153287, ISSN:1873-3581, ORCID:99822858, SCOPUS ID:85111548767
  • Verification of suitable ratio of carbohydrate residues in a glycopolymer having GlcNAc moieties for determining the affinity for wheat germ agglutinin               
    Koji Matsuoka; Shohei Yamashita; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano
    Journal of Molecular Structure, 巻:1217, 開始ページ:128404, 終了ページ:128404, 2020年10月, [査読有り], [筆頭著者, 責任著者]
    Elsevier {BV}, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.molstruc.2020.128404
    DOI ID:10.1016/j.molstruc.2020.128404, ISSN:0022-2860, ORCID:73808680
  • Fluorogenic glycopolymers available for determining the affinity of lectins by intermolecular FRET               
    Koji Matsuoka; Yuya Suzuki; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano
    Bioorganic & Medicinal Chemistry Letters, 巻:30, 号:8, 開始ページ:127024, 終了ページ:127024, 2020年04月, [査読有り], [筆頭著者, 責任著者]
    Elsevier {BV}, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmcl.2020.127024
    DOI ID:10.1016/j.bmcl.2020.127024, ISSN:0960-894X, ORCID:69267177
  • Impaired O-Glycosylation at Consecutive Threonine TTX Motifs in Mucins Generates Conformationally Restricted Cancer Neoepitopes               
    Shun Hayakawa; Takahiko Matsushita; Yasuhiro Yokoi; Hajime Wakui; Fayna Garcia-Martin; Hiroshi Hinou; Koji Matsuoka; Kazuhiro Nouso; Toshiya Kamiyama; Akinobu Taketomi; Shin-Ichiro Nishimura
    Biochemistry, 巻:59, 号:12, 開始ページ:1221, 終了ページ:1241, 2020年03月, [査読有り]
    American Chemical Society ({ACS}), 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1021/acs.biochem.0c00007
    DOI ID:10.1021/acs.biochem.0c00007, ORCID:70874808
  • Neuraminidase-triggered activation of prodrug-type substrate of 4-nitroaniline               
    Takahiko Matsushita; Monique Nami Danyel; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    Bioorganic & Medicinal Chemistry Letters, 巻:30, 号:2, 開始ページ:126883, 終了ページ:126883, 2020年01月, [査読有り], [最終著者, 責任著者]
    Elsevier {BV}, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmcl.2019.126883
    DOI ID:10.1016/j.bmcl.2019.126883, ISSN:0960-894X, ORCID:65788264
  • Self-healing of biobased furan polymers: Recovery of high mechanical strength by mild heating
    Yoshie, N.; Yoshida, S.; Matsuoka, K.
    Polymer Degradation and Stability, 巻:161, 開始ページ:13, 終了ページ:18, 2019年, [査読有り]
    Elsevier {BV}, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.polymdegradstab.2019.01.007
    DOI ID:10.1016/j.polymdegradstab.2019.01.007, ORCID:53133704, SCOPUS ID:85059812231
  • Alcohol-assisted self-healing network polymer based on vicinal tricarbonyl chemistry
    Shintaro Nakagawa; Shuya Nakai; Koji Matsuoka; Naoko Yoshie
    Polymer, 巻:161, 開始ページ:101, 終了ページ:108, 2019年01月, [査読有り]
    Elsevier {BV}, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.polymer.2018.11.061
    DOI ID:10.1016/j.polymer.2018.11.061, ORCID:51269906
  • Synthetic construction of sugar-amino acid hybrid polymers involving globotriaose or lactose and evaluation of their biological activities against Shiga toxins produced by Escherichia coli O157:H7
    Koji Matsuoka; Kiyotaka Nishikawa; Yusuke Goshu; Tetsuo Koyama; Ken Hatano; Takahiko Matsushita; Miho Watanabe-Takahashi; Yasuhiro Natori; Daiyo Terunuma
    Bioorganic & Medicinal Chemistry, 巻:26, 号:22, 開始ページ:5792, 終了ページ:5803, 2018年12月, [査読有り], [筆頭著者, 責任著者]
    Elsevier {BV}, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmc.2018.10.023
    DOI ID:10.1016/j.bmc.2018.10.023, ISSN:0968-0896, ORCID:49967503
  • Preparation of Functional Monomers as Precursors of Bioprobes from a Common Styrene Derivative and Polymer Synthesis
    Riho Hayama; Tetsuo Koyama; Takahiko Matsushita; Ken Hatano; Koji Matsuoka
    Molecules, 巻:23, 号:11, 開始ページ:2875, 終了ページ:2875, 2018年11月, [査読有り], [最終著者, 責任著者]
    CM-Str (4-(Chloromethyl)styrene) was used as a useful starting material for the construction of a series of functional monomers. Substitution of the chlorine to the corresponding azide was performed, and the reduction of the azide proceeded smoothly to afford an aminostyrene, which was used as a common precursor for the preparation of functional monomers. Condensation of the amine with a fluorophore, biotin and carbohydrate was accomplished. Among the monomers, a carbohydrate monomer was polymerized with or without acrylamide as a model polymerization to yield the corresponding water-soluble glycopolymers, and biological evaluations of the glycopolymers for a lectin, and wheat germ agglutinin (WGA), were carried out on the basis of the fluorescence change of tryptophan in the WGA.
    MDPI} {AG, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.3390/molecules23112875
    DOI ID:10.3390/molecules23112875, eISSN:1420-3049, ORCID:50216887
  • A constraint scaffold enhances affinity of a bivalent N-acetylglucosamine ligand against wheat germ agglutinin               
    Takahiko Matsushita; Koji Tsuchibuchi; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    Bioorganic and Medicinal Chemistry Letters, 巻:28, 号:10, 開始ページ:1704, 終了ページ:1707, 2018年06月, [査読有り], [最終著者, 責任著者]
    Bivalent glycoconjugates have a minimal valence with avidity potential on protein-carbohydrate interactions as well as simplicity of chemical structures enabling simple synthesis with low cost. Understanding the way to maximize the affinities of bivalent glycoconjugates is important for the development of cost-effective tools for therapeutic and diagnostic research. However, there has been little discussion about the effects of constraints imposed from ligand scaffolds on the binding abilities. We synthesized three kinds of biantennary N-acetylglucosamine glycosides with different scaffolds using isobutenyl bis(propargyl)ether as a common scaffold precursor. Decoration of the scaffold branches with GlcNAc moieties through copper-catalyzed azide-alkyne cycloaddition and grafting of the alkenyl focal point to another bivalent biotin dendron through thiol-ene and nucleophilic substitution reactions were successfully carried out in an orthogonal manner. The association constants of the ligands against wheat germ agglutinin were determined by a fluorometric titration assay. A bivalent biotin counterpart provided higher affinity than an isobutyl scaffold, whereas an isobutenyl scaffold yielded more enhancement than a bivalent biotin counterpart. The present work suggested that the constraint and steric bulk of ligand scaffolds are possible factors for improving binding properties of glycoconjugates against lectins or proteins.
    Elsevier Ltd, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmcl.2018.04.047
    DOI ID:10.1016/j.bmcl.2018.04.047, ISSN:1464-3405, ORCID:50245771, SCOPUS ID:85046171118, Web of Science ID:WOS:000432729000005
  • 2-Benzoylpyridine Ligand Complexation with Gold Critical for Propargyl Ester-Based Protein Labeling               
    Lin, Y. X.; Vong, K.; Matsuoka, K.; Tanaka, K.
    Chemistry-a European Journal, 巻:24, 号:42, 開始ページ:10595, 終了ページ:10600, 2018年, [査読有り]
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1002/chem.201802058
    DOI ID:10.1002/chem.201802058, ORCID:50245770, Web of Science ID:WOS:000439925300004
  • DNA-based mutation assay GPMA (genome profiling-based mutation assay): reproducibility, parts-per-billion scale sensitivity, and introduction of a mammalian-cell-based approach               
    Parmila Kumari; Sunita Ghimire Gautam; Misato Baba; Motoki Tsukiashi; Koji Matsuoka; Kiyoshi Yasukawa; Koichi Nishigaki
    JOURNAL OF BIOCHEMISTRY, 巻:162, 号:6, 開始ページ:395, 終了ページ:401, 2017年12月, [査読有り]
    Genome profiling-based mutation assay (GPMA) is, to date, the only DNA sequence-based mutation assay that directly measures DNA alterations induced by mutagens. Here, the all-important congruence of mutagen assignment between DNA-based GPMA and the phenotype-based Ames test (the gold standard of mutagen assays) was confirmed qualitatively and semi-quantitatively by means of 94 chemical species (including previously examined 64). The high sensitivity (on the order of 10 ppb) and reproducibility of GPMA were also corroborated by the match between virtually independent experiments conducted in the distant past (10 years ago) and recently. Meanwhile, a standard experimental framework was established: the conditions of 100 parts per billion (ppb) concentration of a chemical and 15-generation culture of Escherichia coli. Moreover, a mammalian cell line (NIH 3T3) was shown to be suitable as a tester organism for the GPMA approach. Preliminary experimental results suggested that this approach can provide a qualitatively equivalent and quantitatively different mutagen assay results relative to the bacteria-based GPMA (renamed as bGPMA). This finding confirmed the effectiveness of the GPMA approach and indicates that mGPMA is a promising way to detect mammalian-cell mutagens.
    OXFORD UNIV PRESS, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1093/jb/mvx043
    DOI ID:10.1093/jb/mvx043, ISSN:0021-924X, eISSN:1756-2651, ORCID:41456978, Web of Science ID:WOS:000417223600002
  • Iodoacetyl-functionalized pullulan: A supplemental enhancer for single-domain antibody–polyclonal antibody sandwich enzyme-linked immunosorbent assay for detection of survivin               
    Takahiko Matsushita; Hidenao Arai; Tetsuo Koyama; Ken Hatano; Naoto Nemoto; Koji Matsuoka
    Bioorganic & Medicinal Chemistry Letters, 巻:27, 号:21, 開始ページ:4844, 終了ページ:4848, 2017年11月, [査読有り], [最終著者, 責任著者]
    Survivin, an inhibitor of the apoptosis protein family, is a potent tumor marker for diagnosis and prognosis. The enzyme-linked immunosorbent assay (ELISA) is one of the methods that has been used for detection of survivin. However, ELISA has several disadvantages caused by the use of conventional antibodies, and we have therefore been trying to develop a novel ELISA system using camelid single-domain antibodies (VHHs) as advantageous replacements. Here we report a supplemental approach to improve the VHH-polyclonal antibody sandwich ELISA for survivin detection. Iodoacetyl-functionalized pullulan was synthesized, and its thiol reactivity was characterized by a model reaction with L-cysteine. The thiophilic pullulan was applied to an immunoassay as an additive upon coating of standard assay plates with an anti-survivin VHH fusion protein with C-terminal cysteine. The results showed that the mole ratio of the additive to VHH had a significant effect on the consequent response. Mole ratios of 0.07, 0.7, and 7 led to 90% lower, 15% higher, and 69% lower responses, respectively, than the response of a positive control in which no additive was used. The background levels observed in any additive conditions were as low as that of a negative control lacking both VHH and the additive. These results indicate the applicability of the thiol-reactive pullulan as a response enhancer to VHH-based ELISA. (C) 2017 Elsevier Ltd. All rights reserved.
    Elsevier {BV}, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmcl.2017.09.045
    DOI ID:10.1016/j.bmcl.2017.09.045, ISSN:0960-894X, eISSN:1464-3405, ORCID:37252279, Web of Science ID:WOS:000413998900013
  • Total Synthesis of Kehokorins A-E, Cytotoxic p-Terphenyls               
    Shunya Takahashi; Yasuaki Suda; Takemichi Nakamura; Koji Matsuoka; Hiroyuki Koshino
    JOURNAL OF ORGANIC CHEMISTRY, 巻:82, 号:6, 開始ページ:3159, 終了ページ:3166, 2017年03月, [査読有り]
    This paper describes a general method for the synthesis of kehokorins A-E, novel cytotoxic p-terphenyls. 2,4,6-Trihydroxybenzaldehyde served as a common building block for preparation of the central aromatic ring. Construction of their p-terphenyl skeletons was achieved by a stepwise Suzuki-Miyaura coupling, whereas the phenyl-dibenzofuran moiety was built up by an intramolecular Ullmann reaction. Introduction of an L-rhamnose residue into partly protected kehokorin B was performed by the trichloroacetimidate method.
    AMER CHEMICAL SOC, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1021/acs.joc.7b00147
    DOI ID:10.1021/acs.joc.7b00147, ISSN:0022-3263, ORCID:41456982, Web of Science ID:WOS:000397077500035
  • Synthetic Assembly of Mannose Moieties Using Polymer Chemistry and the Biological Evaluation of Its Interaction towards Concanavalin A               
    Deepti Diwan; Kohei Shinkai; Toshihiro Tetsuka; Bin Cao; Hidenao Arai; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    MOLECULES, 巻:22, 号:1, 2017年01月, [査読有り], [最終著者, 責任著者]
    Protein-carbohydrate interactions exhibit myriad intracellular recognition events, so understanding and investigating their specific interaction with high selectivity and strength are of crucial importance. In order to examine the effect of multivalent binding on the specificity of protein-carbohydrate interactions, we synthesized mannose glycosides as a novel type of glycosylated monomer and glycopolymers of polyacrylamide derivatives with -mannose (-Man) by radical polymerization and monitored their strength of interaction with concanavalin A (Con A) by surface plasmon resonance (SPR) detection. In a quantitative test using the Con A-immobilized sensor surface, the kinetic affinity for the synthesized polymers, 8a (K-D = 3.3 x 10(-6) M) and 8b (K-D = 5.3 x 10(-5) M), were concentration-dependent, showing strong, specific molecular recognition abilities with lectin. Our study showed the enhancement in recognition specificity for multivalent saccharides, which is often mediated by cell surface carbohydrate-binding proteins that exhibit weak affinity and broad specificity for the individual ligands.
    MDPI AG, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.3390/molecules22010157
    DOI ID:10.3390/molecules22010157, ISSN:1420-3049, ORCID:41456981, Web of Science ID:WOS:000395473500154
  • Synthesis of 3-phenyldibenzo[b,d]furan-type bioprobes utilizing vialinin B as a structural motif               
    Shunya Takahashi; Yasuaki Suda; Takemichi Nakamura; Koji Matsuoka; Hiroyuki Koshino
    SYNTHETIC COMMUNICATIONS, 巻:47, 号:1, 開始ページ:22, 終了ページ:28, 2017年, [査読有り]
    Vialinin B is a natural 3-phenyldibenzo[b,d]furan product with a powerful inhibitory activity against tumor necrosis factor (TNF)-alpha production. This article describes the synthesis of three types of biotinylated p-terphenyls designed for clarifying the target molecule of vialinin B. Construction of the carbon backbone of the core was accomplished by stepwise Suzuki-Miyaura coupling while the phenyl dibenzofuran moiety was built up by the Ullmann reaction. The biotinyl unit was attached through click chemistry.
    [GRAPHICS]
    .
    TAYLOR & FRANCIS INC, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1080/00397911.2016.1245754
    DOI ID:10.1080/00397911.2016.1245754, ISSN:0039-7911, eISSN:1532-2432, ORCID:41456980, Web of Science ID:WOS:000392820700004
  • Biological Evaluation of Multivalent-Type N-Acetyl-D-Glucosamine (GlcNAc) Conjugates for Wheat Germ Agglutinin (WGA) by the Surface Plasmon Resonance (SPR) Method
    Amrita Kumari, Tetsuo Koyama, Ken Hatano,; Koji Matsuoka
    SOJ Biochemistry, 巻:2, 開始ページ:7, 終了ページ:7, 2017年, [査読有り], [最終著者, 責任著者]
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.15226/2376-4589/2/3/00118
    DOI ID:10.15226/2376-4589/2/3/00118, ORCID:41456977
  • Synthetic assembly of novel avidin-biotin-GlcNAc (ABG) complex as an attractive bio-probe and its interaction with wheat germ agglutinin (WGA)               
    Amrita Kumari; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    BIOORGANIC CHEMISTRY, 巻:68, 開始ページ:219, 終了ページ:225, 2016年10月, [査読有り], [最終著者, 責任著者]
    A tetravalent GlcNAc pendant glycocluster was constructed with terminal biotin through C-6 linker. To acquire the multivalent carbohydrate-protein interactions, we synthesized a glycopolymer of tetrameric structure using N-acetyl-D-glucosamine (GlcNAc) as the target carbohydrate by the use of 4-(4,6-dime thoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as coupling reagent, followed by biotin-avidin complexation leading to the formation of glycocluster of avidin-biotin-GlcNAc conjugate (ABG complex). The dynamic light scattering (DLS) system was implied for size detection and to check the binding affinity of GlcNAc conjugate with a WGA lectin we use fluorometric assay by means of specific excitation of tryptophan at lambda(ex) 295 nm and it was found to be very high K-a similar to 1.39 x 10(7) M-1 in case of ABG complex as compared to GlcNAc only K-a similar to 1.01 x 10(4) M-1 with the phenomenon proven to be due to glycocluster effect. (C) 2016 Elsevier Inc. All rights reserved.
    ACADEMIC PRESS INC ELSEVIER SCIENCE, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bioorg.2016.08.002
    DOI ID:10.1016/j.bioorg.2016.08.002, ISSN:0045-2068, eISSN:1090-2120, ORCID:41456984, Web of Science ID:WOS:000387978400022
  • Synthesis of Fluorinated Polymers and Evaluation of Wettability               
    Tamami Kimura; Maria Carmelita Kasuya; Kenichi Hatanaka; Koji Matsuoka
    MOLECULES, 巻:21, 号:3, 2016年03月, [査読有り], [最終著者, 責任著者]
    Two kinds of fluorinated polymers were synthesized: an acrylate polymer having a fluorinated triethylene glycol as a pendant group (2a) and a fluoroalkyl acrylate polymer (2b). The contact angle of these fluorinated polymers against water, non-fluorinated alcohols and fluorinated alcohols were evaluated. As compared with the fluoroalkyl polymer (2b), fluoroethylene glycol polymer (2a) showed smaller contact angle against water and non-fluorinated alcohols. This supports the proposition that changing the alkyl chain into the ethylene glycol-type chain gave some interaction between etheric oxygen and water or non-fluorinated alcohols. In addition, fluoroalkyl acrylate polymer (2b) showed remarkably low values of critical surface tension.
    MDPI AG, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.3390/molecules21030358
    DOI ID:10.3390/molecules21030358, ISSN:1420-3049, ORCID:41456983, Web of Science ID:WOS:000373802200030
  • L-Fucose-containing arabinogalactan-protein in radish leaves               
    Miho Inaba; Takuma Maruyama; Yoshihisa Yoshimi; Toshihisa Kotake; Koji Matsuoka; Tetsuo Koyama; Theodora Tryfona; Paul Dupree; Yoichi Tsumuraya
    CARBOHYDRATE RESEARCH, 巻:415, 開始ページ:1, 終了ページ:11, 2015年10月, [査読有り]
    The carbohydrate moieties of arabinogalactan-proteins (AGPs) have beta-(1 -> 3)-galactan backbones to which side chains of (1 -> 6)-linked beta-Gal residues are attached through O-6. Some of these side chains are further substituted with other sugars. We investigated the structure of L-Fuc-containing oligosaccharides released from the carbohydrate moieties of a radish leaf AGP by digestion with a-l-arabinofuranosidase, followed by exo-beta-(1 -> 3)-galactanase. We detected a series of neutral beta-(1 -> 6)-galactooligosaccharides branching variously at O-3 of the Gal residues, together with corresponding acidic derivatives terminating in 4-O-methyl-GlcA (4-Me-GlcA) or GlcA at the non-reducing terminals. In neutral oligosaccharides with degree of polymerization (dp) mainly higher than 10, L-Fuc groups were attached through L-Ara residues as the sequence, alpha-L-Fucp-(1 -> 2)-alpha-L-Araf-(1 ->. This sequence was verified by isolation of the pentasaccharide alpha-L-Fuc-(1 -> 2)-alpha-L-Araf-(1 -> 3)-beta-Gal-(1 -> 6)-beta-Gal-(1 -> 6)-Gal upon digestion of the higher oligosaccharides with endo-beta-(1 -> 6)-galactanase. By contrast, in lower polymerized (predominantly dp 4) acidic oligosaccharides, L-Fuc groups were attached directly at the non-reducing terminals through alpha-(1 -> 2)-linkages, resulting in the release of the tetrasaccharides, alpha-L-Fucp-(1 -> 2)-beta-GlcA-(1 -> 6)-beta-Gal-(1 -> 6)-Gal and alpha-L-Fucp-(1 -> 2)-beta-4-Me-GlcA-(1 -> 6)-beta-Gal-(1 -> 6)-Gal. In long acidic oligosaccharides with dp mainly higher than 13, L-Fuc groups localized on branches were attached to the uronic acids directly and/or L-Ara residues as in the neutral oligosaccharides. (C) 2015 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).
    ELSEVIER SCI LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.carres.2015.07.002
    DOI ID:10.1016/j.carres.2015.07.002, ISSN:0008-6215, eISSN:1873-426X, ORCID:41456986, Web of Science ID:WOS:000362889100001
  • Effect of Aglycon Structure on Saccharide Elongation by Cells               
    Tamami Kimura; Maria Carmelita Z. Kasuya; Kenichi Hatanaka; Koji Matsuoka
    CHEMISTRY & BIODIVERSITY, 巻:12, 号:2, 開始ページ:239, 終了ページ:247, 2015年02月, [査読有り], [最終著者, 責任著者]
    Alkyl N-acetyl--D-glucosaminide (GlcNAc primers) with different aglycon moieties were synthesized and used to determine the effect of the aglycon structure on cellular saccharide elongation. Dodecyl N-acetyl--D-glucosaminide (GlcNAc-C12), tridecan-7-yl N-acetyl--D-glucosaminide (GlcNAc-2C6), and pentacosan-13-yl N-acetyl--D-glucosaminide (GlcNAc-2C12) primers were synthesized by glycosylation of dodecan-1-ol, tridecan-7-ol, and pentacosan-13-ol, respectively, with peracetylglucosamine. These primers were introduced to mouse B16 melanoma cells to prepare glycolipids. After 48h incubation, results showed that GlcNAc-C12 was elongated to give NeuAc-Gal-GlcNAc-C12. GlcNAc-2C6 was also elongated to afford Gal-GlcNAc-2C6 and NeuAc-Gal-GlcNAc-2C6. On the other hand, GlcNAc-2C12 primer was not elongated. Significantly, the results demonstrated that the amount of glycosylated product increased 1.5-times by modifying the aglycon structure of GlcNAc from C-12 to 2 C-6 despite having almost the same number of C-units.
    WILEY-V C H VERLAG GMBH, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1002/cbdv.201400278
    DOI ID:10.1002/cbdv.201400278, ISSN:1612-1872, eISSN:1612-1880, ORCID:41456985, Web of Science ID:WOS:000350115000004
  • Synthesis and Structural Revision of a Brominated Sesquiterpenoid, Aldingenin C               
    Shunya Takahashi; Masayuki Yasuda; Takemichi Nakamura; Ken Hatano; Koji Matsuoka; Hiroyuki Koshino
    JOURNAL OF ORGANIC CHEMISTRY, 巻:79, 号:19, 開始ページ:9373, 終了ページ:9380, 2014年10月, [査読有り]
    This paper describes a short step synthesis of the proposed structure for aldingenin C from trans-limonene oxide. The tetrahydropyran-fused 2-oxabicyclo[3.2.2]nonane skeleton as the structural feature was constructed by an intramolecular epoxide-opening reaction and a brominative cyclization. The spectral data of the synthetic compound did not match those of the natural product reported. Re-examination of the reported NMR data using new CAST/CNMR Structure Elucidator suggests that the structure of aldingenin C should be revised to that of known caespitol.
    AMER CHEMICAL SOC, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1021/jo501228v
    DOI ID:10.1021/jo501228v, ISSN:0022-3263, eISSN:1520-6904, ORCID:41456990, Web of Science ID:WOS:000342719600044
  • Synthesis and Influenza Virus Inhibitory Activities of Carbosilane Dendrimers Peripherally Functionalized with Hemagglutinin-Binding Peptide               
    Ken Hatano; Teruhiko Matsubara; Yosuke Muramatsu; Masakazu Ezure; Tetsuo Koyama; Koji Matsuoka; Ryunosuke Kuriyama; Haruka Kori; Toshinori Sato
    JOURNAL OF MEDICINAL CHEMISTRY, 巻:57, 号:20, 開始ページ:8332, 終了ページ:8339, 2014年10月, [査読有り]
    A series of carbosilane dendrimers uniformly functionalized with hemagglutinin (HA) binding peptide (sialic acid-mimic peptide, Ala-Arg-Leu-Pro-Arg) was systematically synthesized, and their anti-influenza virus activity was evaluated. The carbosilane-based peptide dendrimers, unlike sialylated dendrimers, cannot be digested by virus neuraminidases. The peptide dendrimers exhibited intriguing biological activities depending on the form of their core frame, with a dumbbell-type peptide dendrimer showing particularly strong inhibitory activities against two human influenza viruses, A/PR/8/34 (H1N1) and A/Aichi/2/68 (H3N2). The IC50 values of the dumbbell-type peptide dendrimer for both strains were 0.60 mu M, the highest activity among the HA-binding peptide derivatives. The results suggest that a dumbbell-shaped carbosilane dendrimer is the most suitable core scaffold for HA-binding peptide dendrimers.
    AMER CHEMICAL SOC, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1021/jm5007676
    DOI ID:10.1021/jm5007676, ISSN:0022-2623, eISSN:1520-4804, ORCID:41456989, Web of Science ID:WOS:000343740700011
  • Structural revision of kynapcin-12 by total synthesis, and inhibitory activities against prolyl oligopeptidase and cancer cells               
    Shunya Takahashi; Ayaka Yoshida; Shota Uesugi; Yayoi Hongo; Ken-ichi Kimura; Koji Matsuoka; Hiroyuki Koshino
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 巻:24, 号:15, 開始ページ:3373, 終了ページ:3376, 2014年08月, [査読有り]
    Kynapcin-12 is a prolyl oligopeptidase (POP) inhibitor isolated from Polyozellus multiplex, and its structure was assigned as 1 having a p-hydroquinone moiety by spectroscopic analyses and chemical means. This Letter describes the total syntheses of the proposed structure 1 for kynapcin-12 and 2',3'-diacetoxy-1,5',6',4 ''-tetrahydroxy-p-terphenyl 2 isolated from Boletopsis grisea, revising the structure of kynapcin-12 to the latter. These syntheses involved double Suzuki-Miyaura coupling, CAN oxidation, and LTA oxidation as key steps. The inhibitory activities of synthetic compounds against POP and cancer cells were also evaluated. (C) 2014 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmcl.2014.05.091
    DOI ID:10.1016/j.bmcl.2014.05.091, ISSN:0960-894X, eISSN:1464-3405, ORCID:41456988, Web of Science ID:WOS:000339228700030
  • Use of chloromethylstyrene as a supporter for convenient preparation of carbohydrate monomer and glycopolymers               
    Koji Matsuoka; Anna Kurita; Tetsuo Koyama; Ken Hatano
    CARBOHYDRATE POLYMERS, 巻:107, 開始ページ:209, 終了ページ:213, 2014年07月, [査読有り], [筆頭著者, 責任著者]
    A convenient access for glycopolymers was accomplished by using a styrene-modified glycomonomer, which was prepared from chloromethylstyrene as a key starting material and N-acetyl-D-glucosamine (GlcNAc) as a model carbohydrate. One-step conversion of the styrene derivative gave an azidostyrene, which was treated with a propargyl GlcNAc to afford a carbohydrate monomer after deprotection in good yield. The water-soluble GlcNAc monomer was polymerized with or without acrylamide to give the corresponding white powdery glycopolymers, which were evaluated for their interaction against wheat germ agglutinin (WGA) on the basis of fluorescence change of tryptophan in WGA. (C) 2014 Elsevier Ltd. All rights reserved.
    ELSEVIER SCI LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.carbpol.2014.01.104
    DOI ID:10.1016/j.carbpol.2014.01.104, ISSN:0144-8617, eISSN:1879-1344, ORCID:41456992, Web of Science ID:WOS:000335103900027
  • Synthesis of chiral dopants based on carbohydrates               
    Toru Tsuruta; Tetsuo Koyama; Mikio Yasutake; Ken Hatano; Koji Matsuoka
    CARBOHYDRATE RESEARCH, 巻:393, 開始ページ:15, 終了ページ:22, 2014年07月, [査読有り], [最終著者]
    Chiral dopants based on carbohydrates for nematic liquid crystals were synthesized from D-glucose, and their helical twisting power (HTP) values were evaluated. The chiral dopants induced helices in the host nematic liquid crystals. An acetyl derivative having an ether-type glycosidic linkage between carbohydrate and a mesogenic moiety showed the highest HTP value of 10.4 mu m (1), while an acetyl derivative having an anomeric ester-type linkage did not show any HTP. It was surprising that this molecule had no HTP despite the presence of chirality in the molecule. A relationship between HTP and specific rotation was not observed in this study. (C) 2014 Elsevier Ltd. All rights reserved.
    ELSEVIER SCI LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.carres.2014.04.007
    DOI ID:10.1016/j.carres.2014.04.007, ISSN:0008-6215, eISSN:1873-426X, ORCID:41456991, Web of Science ID:WOS:000338714300003
  • Enzymatic fragmentation of carbohydrate moieties of radish arabinogalactan-protein and elucidation of the structures               
    Ryohei Shimoda; Kohei Okabe; Toshihisa Kotake; Koji Matsuoka; Tetsuo Koyama; Theodora Tryfona; Hui-Chung Liang; Paul Dupree; Yoichi Tsumuraya
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 巻:78, 号:5, 開始ページ:818, 終了ページ:831, 2014年05月, [査読有り]
    We investigated the structures of L-arabino-galactooligosaccharides released from the sugar moieties of a radish arabinogalactan-protein (AGP) by the action of exo-beta-(1 -> 3)-galactanase. We detected a series of neutral beta-(1 -> 6)-linked galactooligosaccharides forming branches of one to up to at least 19 consecutive Gal groups, together with corresponding acidic derivatives terminating in 4-O-methyl-glucuronic acid (4-Me-GlcA) at the non-reducing end. Some oligosaccharide chains of degree of polymerization (dp) higher than 3 for neutral, and 4 for acidic oligomers were modified with L-Araf residues. The acidic tetrasaccharide 4-Me-beta-GlcA-(1 -> 6)[alpha-L-Araf-(1 -> 3)]-beta-Gal-(1 -> 6)-Gal was detected as an abundant L-Araf-containing oligosaccharide among these neutral and acidic oligomers. A pentasaccharide containing an additional L-Araf group attached to the L-Ara in the tetrasaccharide through an alpha-(1 -> 5)-linkage was also found. We observed L-ara-bino-galactooligosaccharides substituted with single or disaccharide L-Araf units at different Gal residues along these neutral and acidic beta-(1 -> 6)-galactooligosaccharide chains, indicating that these side chains are highly variable in length and substituted variously with L-Araf residues.
    TAYLOR & FRANCIS LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1080/09168451.2014.910100
    DOI ID:10.1080/09168451.2014.910100, ISSN:0916-8451, eISSN:1347-6947, ORCID:41456987, Web of Science ID:WOS:000339070600015
  • Carbosilane glycodendrimers               
    Ken Hatano; Koji Matsuoka; Daiyo Terunuma
    Chemical Society Reviews, 巻:42, 号:11, 開始ページ:4574, 終了ページ:4598, 2013年06月, [査読有り]
    Glycodendrimers fascinate both carbohydrate chemists and biologists because of their ability to recognize lectins and enhance carbohydrate-protein interactions. These characteristics make glycodendrimers a valuable tool in glycoscience and chemical biology. Many glycodendrimers have been described to date
    this tutorial review focuses specifically on carbosilane glycodendrimers. We present methodologies for synthesizing parent carbosilane dendrimers and describe their use in biological assays. We also describe representative functionalizations of parent carbosilane dendrimers at terminal positions which are necessary for chemical ligation with carbohydrate ligands. This is followed by a description of all coupling reactions between carbohydrate and carbosilane dendrimer functionalities used in the synthesis of carbosilane glycodendrimers. The major emphasis of this review is the use of carbosilane glycodendrimers as medical agents against Shiga toxins, dengue viruses, relapsing fever Borrelia, and hemagglutinin and neuraminidase of influenza viruses, as well as on the relationship between dendrimer structure and these biological activities. The last two sections introduce recent attempts to use carbosilane glycodendrimers as new versatile and widely-applicable lectin sensors, and the use of carbosilane glycodendrimers as a novel drug carrier in an active targeting drug delivery system. This review article will be of interest to scientists in the areas of organic chemistry, chemical biology, carbohydrate chemistry, heteroatom chemistry, and organosilicon chemistry. © 2013 The Royal Society of Chemistry.
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1039/c2cs35421g
    DOI ID:10.1039/c2cs35421g, ISSN:0306-0012, ORCID:41456994, PubMed ID:23257960, SCOPUS ID:84877819735, Web of Science ID:WOS:000318791200006
  • Inhibitory effects and specificity of synthetic sialyldendrimers toward recombinant human cytosolic sialidase 2 (NEU2)               
    M. Motiur Rahman; Satoshi Kitao; Daisuke Tsuji; Kaori Suzuki; Jun-Ichi Sakamoto; Koji Matsuoka; Fumiko Matsuzawa; Sei-Ichi Aikawa; Kohji Itoh
    GLYCOBIOLOGY, 巻:23, 号:4, 開始ページ:495, 終了ページ:504, 2013年04月, [査読有り]
    Human sialidase 2 (NEU2) is a cytoplasmic sialidase that degrades sialylglycoconjugates, including glycoproteins and gangliosides, via hydrolysis of terminal sialic acids to produce asialo-type molecules. Here, we first report the inhibitory effects of a series of synthetic sialyldendrimers comprising three types [Dumbbell(1)6-S-Neu5Ac(6), Fan(0)3-S-Neu5Ac(3) and Ball(0)4-S-NeuAc(4)] toward recombinant human NEU2 in vitro. Among them, Dumbbell(1)6-S-Neu5Ac(6) exhibited the most potent inhibitory activity (concentration causing 50% inhibition (IC50), 0.4 similar to 0.5 mM). In addition, NeuSLac and NeuSCel carrying thiosialyltrisaccharide moieties exhibited more potent inhibitory effects than NeuSGal and NeuSGlc carrying thiosialyldisaccharides. Docking models composed of NEU2 and the thiosialyloligosaccharide suggested that the active pocket of NEU2 prefers the second galactose-beta (Gal beta) to the glucose-beta (Glc beta) residue in the trisaccharide structure, there being a hydrogen bond between the 4-hydroxy group of the second Gal beta and the side chain of the D46 residue of NEU2. The third Glc beta residues of NeuSLac and NeuSCel were also predicted to be stabilized by hydrogen bonds with the side chains of the R21, R304, D358 and Y359 residues of NEU2. NEU2 mutants (D358A and Y359A) exhibited reduced affinity for NeuSLac carrying thiosialyltrisaccharide moieties, suggesting the significant roles of D358 and Y359 residues in recognition of thiosialyltrisaccharide moieties of NeuSLac bound in the active pocket of NEU2. Thus, the present sialyldendrimers could be utilized not only as a new class of NEU2 inhibitors but also as molecular probes for evaluating the biological functions of NEU2, including the catalytic activity and mechanism as to natural substrates carrying sialyloligosaccharides.
    OXFORD UNIV PRESS INC, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1093/glycob/cws221
    DOI ID:10.1093/glycob/cws221, ISSN:0959-6658, ORCID:41456996, Web of Science ID:WOS:000315631900008
  • Carbohydrate immobilized on a dendrimer-coated colloidal gold surface for fabrication of a lectin-sensing device based on localized surface plasmon resonance spectroscopy               
    Masayo Ogiso; Junko Kobayashi; Tomoko Imai; Koji Matsuoka; Miki Itoh; Takeshi Imamura; Tomoko Okada; Hiroshi Miura; Toshinori Nishiyama; Kenichi Hatanaka; Norihiko Minoura
    Biosensors and Bioelectronics, 巻:41, 号:1, 開始ページ:465, 終了ページ:470, 2013年03月, [査読有り]
    Carbohydrate-mediated functions in biological systems have generated considerable interest in recent years. We have developed a device bearing immobilized carbohydrates on a colloidal gold surface and applied this device to the detection of carbohydrate-binding molecules by using localized surface plasmon resonance (LSPR) spectroscopy. The sensing device was constructed by using cyanuric chloride as an amine-linker between an amino residue of a polyamidoamine (PAMAM) dendrimer-coated colloidal gold surface and the amino residue of a 12-aminododecyl glycoside. After optimizing the construction of the device, we characterized its LSPR-based sensing capability. Binding specificity with lectins and linear range responses were obtained with the device. Our LSPR-based sensing device thus provides a label-free, low-cost detection method for use as a laboratory research tool or in medical glycan arrays. © 2012 Elsevier B.V.
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bios.2012.09.003
    DOI ID:10.1016/j.bios.2012.09.003, ISSN:0956-5663, ORCID:41456993, PubMed ID:23036773, SCOPUS ID:84870770998, Web of Science ID:WOS:000314191300069
  • Immobilization of carbohydrate clusters on a quartz crystal microbalance sensor surface               
    Masayo Ogiso; Koji Matsuoka; Tomoko Okada; Tomoko Imai; Miki Itoh; Takeshi Imamura; Yoshimi Haga; Kenichi Hatanaka; Norihiko Minoura
    Journal of Colloid and Interface Science, 巻:393, 号:1, 開始ページ:257, 終了ページ:263, 2013年03月, [査読有り]
    The immobilization of carbohydrates on gold surfaces is a prerequisite technology for carbohydrate-related studies, including those of carbohydrate-biomolecule interactions. Glycolipid domains in cell membranes, such as lipid rafts, are thought to play an important role in cell biology through their carbohydrate portions. To understand the recognition of glycolipid domains such as receptors for bacterial toxins and viruses, we immobilized clusters of carbohydrates on a gold surface by using polyamidoamine (PAMAM) dendrimers as a scaffold. The PAMAM dendrimers were adsorbed on the gold-coated surface of a quartz crystal microbalance (QCM) sensor and were observed by means of QCM with dissipation (QCM-D). After adsorption of the PAMAM dendrimers, lysoganglioside-GM1 and 12-aminododecyl-N-acetylglucosaminide (GlcNAc-C12-NH2) were immobilized on the amino groups of PAMAM dendrimers by means of an NH2 cross-linker. Immobilization of the carbohydrates was confirmed by observation of their specific interaction with anti-ganglioside GM1 antibody or wheat germ agglutinin (WGA). Surfaces with different GlcNAc-C12-NH2 cluster sizes and densities were prepared by varying the size of the PAMAM dendrimers or the concentration of GlcNAc-C12-NH2 immobilized on the dendrimers, respectively. Analysis of the binding between the GlcNAc-C12-NH2-immobilized surface and WGA revealed that the size of the PAMAM dendrimers influenced the GlcNAc-C12-NH2-WGA interaction, with larger dendrimers resulting in higher WGA binding constants. © 2012 Elsevier Inc.
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.jcis.2012.10.056
    DOI ID:10.1016/j.jcis.2012.10.056, ISSN:0021-9797, ORCID:41456995, PubMed ID:23200344, SCOPUS ID:84873060400, Web of Science ID:WOS:000314666300033
  • Total synthesis of the proposed structure for pochonicine and determination of its absolute configuration               
    Kitamura Y; Koshino H; Nakamura T; Tsuchida A; Nitoda T; Kanzaki H; Matsuoka K; Takahashi S
    Tetrahedron Letters, 巻:54, 号:11, 開始ページ:1456, 終了ページ:1459, 2013年, [査読有り]
    Pochonicine is a polyhydroxylated pyrrolizidine alkaloid with a powerful inhibitory activity against beta-N-acetylglucosaminidases. The proposed structure for pochonicine and the three diastereomers concerning its C-1 and/or C-3 positions were synthesized from N-acetyl-D-glucosamine through construction of the pyrrolizidine skeleton by two intramolecular amino cyclizations as key steps. This synthetic study not only revised the structure of the natural product to the corresponding 1,3-di-epi-form but also determined the absolute configuration as 1R, 3S, 5R, 6R, 7S, 7aR. (C) 2013 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tetlet2013.01.015
    DOI ID:10.1016/j.tetlet2013.01.015, ISSN:0040-4039, ORCID:41456998, Web of Science ID:WOS:000315306900030
  • Probing Single-Molecule Enzymatic Dynamics of B-Glucosidase using Zero-Mode Waveguides
    Ryo Iizuka; Ikumi Toshimitsu; Kentaro Tahara; Hirokatsu Arai; Toshihiro Tetsuka; Koji Matsuoka; Shou Ryu; Yuji Asano; Takashi Tanii; Kiyohiko Igarashi; Masahiro Samejima; Takashi Funatsu
    BIOPHYSICAL JOURNAL, 巻:104, 号:2, 開始ページ:178A, 終了ページ:178A, 2013年01月, [査読有り]
    CELL PRESS, 英語, 研究論文(国際会議プロシーディングス)
    ISSN:0006-3495, ORCID:41456997, Web of Science ID:WOS:000316074301410
  • Convenient assembly of trimeric Le(x) determinants using carbosilane scaffolds by means of Huisgen cycloaddition               
    Koji Matsuoka; Hiroki Yamaguchi; Tatsuya Kohzu; Jun-Ichi Sakamoto; Tetsuo Koyama; Ken Hatano; Shigeto Yamamoto; Tsutomu Mori; Kenichi Hatanaka
    TETRAHEDRON LETTERS, 巻:53, 号:50, 開始ページ:6793, 終了ページ:6796, 2012年12月, [査読有り], [筆頭著者, 責任著者]
    The Le(x) glycoside having an N-3 moiety at the omega position, which was prepared by using living cells from GlcNAcO(CH2)(12)N-3 as a starting material, was efficiently introduced into a trivalent-type carbosilane core scaffold by means of Huisgen cycloaddition reaction to yield the corresponding glycocluster having three Le(x) moieties at each end. Structural elucidation of the product was performed by a combination of NMR and mass spectroscopic analyses, and the results of the analyses supported the structure of the glycocluster. Evaluation of the glycocluster was carried out using Lotus lectin as a model lectin. Environmental changes of tryptophan residues located at or near the binding sites of Lotus lectin caused fluorescence intensity change. (C) 2012 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tetlet.2012.10.004
    DOI ID:10.1016/j.tetlet.2012.10.004, ISSN:0040-4039, ORCID:41457001, Web of Science ID:WOS:000311473500016
  • Influence of passage number on glycosylation of alkyl lactosides by Madin-Darby canine kidney (MDCK) cells               
    Yumiko Shimura; Junya Suzuki; Maria Carmelita Zulueta Kasuya; Koji Matsuoka; Kenichi Hatanaka
    JOURNAL OF BIOSCIENCE AND BIOENGINEERING, 巻:114, 号:5, 開始ページ:552, 終了ページ:555, 2012年11月, [査読有り]
    The cell function on saccharide biosynthesis can be evaluated by employing the saccharide primer method. This study demonstrated that the characteristics of Madin-Darby canine kidney (MDCK) cells changed in relation with passage number when 12-azidododecyl beta-lactoside (Lac-12N(3) primer) was incorporated into MDCK cells and afforded GM3-, GD3-, sialylparagloboside (SPG), and NeuAc-Gal-GlcNAc-Gal-GIcNAc-Lac-type oligosaccharides. By measuring the amount of glycosylated products from relatively early to late passage numbers, results showed that there was an appropriate passage number that optimized oligosaccharide production and that the higher passage number resulted to a decrease in oligosaccharide production. Moreover, results suggested that aside from sialyltransferase, the activity of several kinds of enzymes that control the amount of saccharide production was presumably affected depending upon the biological senescence. (C) 2012, The Society for Biotechnology, Japan. All rights reserved.
    SOC BIOSCIENCE BIOENGINEERING JAPAN, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.jbiosc.2012.06.007
    DOI ID:10.1016/j.jbiosc.2012.06.007, ISSN:1389-1723, ORCID:41457002, Web of Science ID:WOS:000312630000015
  • A carbosilane dendrimer and a silacyclopentadiene analog carrying peripheral lactoses as drug-delivery systems               
    Hiroaki Aizawa; Kentaro Otomo; Nobuaki Honsho; Tomoyuki Shimazaki; Masumi Villeneuve; Koji Matsuoka; Ken Hatano; Daiyo Terunuma
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 巻:22, 号:10, 開始ページ:3564, 終了ページ:3566, 2012年05月, [査読有り]
    A carbosilane dendrimer (4a) and its silacyclopentadiene analog (4b), both functionalized with lactoses, were tested for their abilities to act as drug-delivery systems. The critical micelle concentrations of 4a and 4b were measured using the drop-volume method in water and were 1.7 and 2.9 mu M, respectively, suggesting that they could act as aggregates of glycoclusters. The amounts of the hydrophobic dye Orange OT loaded onto aqueous micelles of 4a and 4b and the stabilities of the dye/micelle complexes were determined by extracting the dyes from the complexes into chloroform. The particle sizes were measured for the loaded micelles by dynamic light scattering. Transfer of the dye from the micelles to peanut agglutinin was observed by fluorescence microscopy. Given the abilities of micelles of 4a and 4b to bind and release Orange OT, these glycocluster micelles may find use as drug-delivery systems. (C) 2012 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmcl.2012.03.034
    DOI ID:10.1016/j.bmcl.2012.03.034, ISSN:0960-894X, ORCID:41456999, Web of Science ID:WOS:000303545900035
  • Lectin Detection Based on the Aggregation-Induced Emission Effect               
    Ken Hatano; Koji Matsuoka; Daiyo Terunuma
    TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY, 巻:24, 号:136, 開始ページ:78, 終了ページ:94, 2012年03月, [査読有り]
    Effective tests for detecting a virus are important because of the increased risk of exposure to newly emerging and highly infectious pathogens due to global warming and increasing international travel. Time-consuming and highly sensitive methods for detection enable a pathogen to be detected during the early phase of infection; however, simple and quick detection testing that can be performed anywhere is often required, particularly in the case of high infectability and mortal diseases. In this review, we introduce a synthetic approach and optical property of a novel lectin detection utilizing carbohydrate-protein-specific recognition and aggregation-induced emission effect though a few examples and also discuss the emission mechanism.
    GAKUSHIN PUBL CO, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.4052/tigg.24.78
    DOI ID:10.4052/tigg.24.78, ISSN:0915-7352, ORCID:41457005, Web of Science ID:WOS:000305623400003
  • Synthetic Assembly of Bifluorescence-Labeled Glycopolymers as Substrates for Assaying alpha-Amylase by Resonance Energy Transfer               
    Koji Matsuoka; Hirokatsu Arai; Hiroyuki Oka; Tetsuo Koyama; Ken Hatano
    ACS MACRO LETTERS, 巻:1, 号:2, 開始ページ:266, 終了ページ:269, 2012年02月, [査読有り], [筆頭著者, 責任著者]
    To meet the need for a convenient substrate for sensitive and continuous assay for alpha-amylase, we developed a fluorescence resonance energy transfer (FRET)-based polymer substrate. Radical copolymerization of FRET-component monomers in different ratios of fluorogenic donor and acceptor was utilized to prepare such polymers. A glycomonomer as a fluorogenic donor was derived from naphthylmethylated maltotetraose, and a dansyl derivative monomer was used as an acceptor. Their mixture and acryl amide were copolymerized in a typical radical polymerization to yield a bifluorescence-labeled polymer in good yield. All of the polymers showed effective FRET and were used for the continuous assay, of human salivary alpha-amylase. The time course of alpha-amylase reactions led to the apparent kinetic parameters of K-m = 4 mu M and V-max = 0.29 nmol/min. The results strongly suggested that FRET-sensitive polymers are conveniently accessible and applicable for the sensitive determination of biochemical events.
    AMER CHEMICAL SOC, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1021/mz200135y
    DOI ID:10.1021/mz200135y, ISSN:2161-1653, ORCID:41457007, Web of Science ID:WOS:000301969500003
  • Glyco-silicon functional materials as anti-influenza virus agents               
    Koji Matsuoka; Tetsuo Koyama; Ken Hatano
    Open Glycoscience, 巻:5, 号:1, 開始ページ:31, 終了ページ:40, 2012年, [査読有り], [筆頭著者, 責任著者]
    This review shows introduction of glycoclusters using carbosilanes as core scaffolds, preparations of glyco-clusters and their excellent properties as well as functions. Since a dendrimer has unique advantages such as single mo-lecular weight, regularity of structure and easy control of shape and size, dendrimers are utilized in various research areas. Results of syntheses and biological evaluations of the carbosilane dendrimers having carbohydrate moieties for influenza viruses are presented. © Matsouka et al.
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.2174/1875398101205010031
    DOI ID:10.2174/1875398101205010031, ISSN:1875-3981, SCOPUS ID:84861876640
  • Synthetic studies of bi-fluorescence-labeled maltooligosaccharides as substrates for alpha-amylase on the basis of fluorescence resonance energy transfer (FRET)               
    Hiroyuki Oka; Tetsuo Koyama; Ken Hatano; Koji Matsuoka
    BIOORGANIC & MEDICINAL CHEMISTRY, 巻:20, 号:1, 開始ページ:435, 終了ページ:445, 2012年01月, [査読有り], [最終著者, 責任著者]
    A series of bi-fluorescence-labeled maltooligosaccharides that lead to fluorescence resonance energy transfer (FRET) was systematically synthesized. Effective FRETs were observed with all of the synthesized probes. Digestion of probes having tetra-, quintet-, hexa- or hepta-saccharidic chain lengths with human saliva alpha-amylase resulted in disappearance of FRET when an excitation wavelength of at 290 nm was used followed by detection at ca. 520 nm due to emission from the dansyl moiety. However, continuous FRET was observed when probes having di- or trisaccharidic chain lengths were used as substrates. In addition to the substrate characteristics based on saccharidic chain length, the reaction rates of digestion for the substrates by amylase were different and also depended on their saccharidic chain length. (C) 2011 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmc.2011.10.065
    DOI ID:10.1016/j.bmc.2011.10.065, ISSN:0968-0896, ORCID:41457008, Web of Science ID:WOS:000298633300047
  • Synthesis and biological evaluation of sialic acid derivatives containing a long hydrophobic chain at the anomeric position and their C-5 linked polymers as potent influenza virus inhibitors               
    Kaori Suzuki; Tetsuo Koyama; Sangchai Yingsakmongkon; Yasuo Suzuki; Ken Hatano; Koji Matsuoka
    BIOORGANIC & MEDICINAL CHEMISTRY, 巻:20, 号:1, 開始ページ:446, 終了ページ:454, 2012年01月, [査読有り], [最終著者, 責任著者]
    Conversions of the C-5 acetamide group in sialic acid into two kinds of C=C double bond substituents were accomplished under Shotten-Baumann conditions. The polymerizable glycomonomers also contain a hydrophobic chain or hydroxyl group at the anomeric position. Radical polymerizations of the fully protected glycomonomers were carried out with acryl amide in the presence of ammonium persulfate (APS) and N,N,N',N'-tetramethylethylenediamine (TEMED), followed by deprotection to furnish water-soluble glycopolymers. The activities of the deprotected glycopolymers and glycomonomers against human influenza viruses (H1N1 and H3N2) and avian influenza virus (H5N3) were evaluated. Biological evaluations showed that the glycomonomers containing a long hydrophobic chain at the anomeric position had both hemagglutination and neuraminidase inhibitory activities. (C) 2011 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmc.2011.10.064
    DOI ID:10.1016/j.bmc.2011.10.064, ISSN:0968-0896, ORCID:41457006, Web of Science ID:WOS:000298633300048
  • LARGE SCALE BIOSYNTHESIS OF GANGLIOSIDE ANALOGUES BY RERF-LC-AI CELLS CULTURED IN HYPERFlask               
    Yumiko Shimura; Junya Suzuki; Miho Muraoka; Maria Carmelita Zulueta Kasuya; Koji Matsuoka; Kenichi Hatanaka
    PREPARATIVE BIOCHEMISTRY & BIOTECHNOLOGY, 巻:42, 号:4, 開始ページ:378, 終了ページ:392, 2012年, [査読有り]
    The efficient production of ganglioside analogues was accomplished using RERF-LC-AI cells cultured in HYPERFlask (High Yield PERformance Flask). Eight kinds of ganglioside analogues (GM3, GM2, sialylparagloboside, GD3, di-sialylated lacto-N-tetraose, and another three kinds of analogues with intricate structures) were synthesized by the saccharide primer method using lung squamous-cell carcinoma line RERF-LC-AI and 12-azidododecyl beta-lactoside primer. The yield for each analogue obtained using HYPERFlask was higher than yields obtained from 100- mm dishes.
    TAYLOR & FRANCIS INC, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1080/10826068.2011.627971
    DOI ID:10.1080/10826068.2011.627971, ISSN:1082-6068, ORCID:41457004, Web of Science ID:WOS:000305515200007
  • Intricate Recognition of Glycolipid-Like Compounds by HIV-1 Envelope Proteins Evaluated with Surface Plasmon Resonance Imaging               
    Tomoko Okada; Arisa Kimura; Hiroshi Miura; Toshinori Nishiyama; Masako Mori; Jyunya Suzuki; Masayo Ogiso; Koji Matsuoka; Toshinori Sato; Kenichi Hatanaka; Norihiko Minoura
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 巻:31, 号:7, 開始ページ:584, 終了ページ:592, 2012年, [査読有り]
    Fusion of human immunodeficiency virus (HIV) to the cell membrane occurs by the specific binding of an envelope protein of HIV-1 (gp120 and gp160) and a glycosphingolipid of the cell membrane. In this study, quantitative and array-based affinity evaluation of gp120 and gp160 was performed by surface plasmon resonance (SPR) and the SPR imaging technique using a substrate immobilized with glycolipid-like compounds (Gb3, GM3, and Lac). Quantitative affinity evaluation showed that gp160 specifically bound to Gb3 and Lac compared with GM3, whereas gp120 showed lower binding affinity and specificity. Array-based evaluation showed that gp160 binds to Gb3 more favorably than Lac and GM3.
    TAYLOR & FRANCIS INC, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1080/07328303.2012.682190
    DOI ID:10.1080/07328303.2012.682190, ISSN:0732-8303, ORCID:41457003, Web of Science ID:WOS:000308250400004
  • A Novel Method for the Production of Glycosphingolipids               
    Yumiko Shimura; Junya Suzuki; Maria Carmelita Z. Kasuya; Koji Matsuoka; Kenichi Hatanaka
    HELVETICA CHIMICA ACTA, 巻:95, 号:1, 開始ページ:67, 終了ページ:75, 2012年01月, [査読有り]
    Neolacto-series ganglioside sialylparagloboside (SPG) is a ganglioside species present in various human tissues, and used in many important studies. In this study, four ganglioside analogs, GM3, GD3, SPG, and NeuAc-Gal-GlcNAc-Gal-GlcNAc-Gal-Glc-Cer, were synthesized by the saccharide-primer method using MDCK cells and beta-lactoside primer with different aglycons. As compared to former methods for producing SPG, the primer method was rapid and convenient. Moreover, the yield of SPG was much higher than that obtained by former methods. The production of gangliosides with an azido group in the aglycon moiety was also achieved by using MDCK cells.
    WILEY-V C H VERLAG GMBH, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1002/hlca.201100246
    DOI ID:10.1002/hlca.201100246, ISSN:0018-019X, ORCID:41457000, Web of Science ID:WOS:000299160000007
  • その場で診断できる感染症検査薬をめざして(レーダー)               
    幡野 健; 松岡 浩司
    化学と教育, 巻:59, 号:11, 開始ページ:560, 終了ページ:561, 2011年, [招待有り]
    公益社団法人 日本化学会, 日本語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.20665/kakyoshi.59.11_560
    DOI ID:10.20665/kakyoshi.59.11_560, ISSN:0386-2151, CiNii Articles ID:110008898224, CiNii Books ID:AN10033386
  • Synthesis of sialyllactosamine clusters using carbosilane as core scaffolds by means of chemical and enzymatic approaches               
    Koji Matsuoka; Reina Kaneko; Tetsuo Koyama; XiaoTao Ma; Yasuaki Esumi; Takemichi Nakamura; Ken Hatano; Daiyo Terunuma
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 巻:20, 号:16, 開始ページ:4906, 終了ページ:4910, 2010年08月, [査読有り], [筆頭著者, 責任著者]
    An efficient synthesis of sialyllactosamine (SiaLacNAc) clusters using carbosilanes as core scaffolds has been accomplished by means of chemical and enzymatic approaches. N-Acetyl-D-glucosamine (GlcNAc) clusters having O-glycosidic linkage or S-glycosidic linkage were chemically synthesized from known intermediates in high yields. The GlcNAc clusters were first used as substrates for beta 1,4 galactosyl transferase using UDP-galactose (UDP-Gal) as a sugar source to provide corresponding N-acetyllactosamine clusters. Further sugar elongation of the LacNAc clusters was demonstrated using alpha 2,3 sialyl transferase and CMP-neuraminic acid (CMP-NANA) to yield the corresponding SiaLacNAc clusters. (c) 2010 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmcl.2010.06.066
    DOI ID:10.1016/j.bmcl.2010.06.066, ISSN:0960-894X, eISSN:1464-3405, ORCID:41457011, Web of Science ID:WOS:000280348400038
  • Synthetic construction of a fucosyl chitobiose as an allergen-associated carbohydrate epitope and the glycopolymer involving highly clustered trisaccharidic sequences               
    Koji Matsuoka; Hiroki Yamaguchi; Tetsuo Koyama; Ken Hatano; Daiyo Terunuma
    TETRAHEDRON LETTERS, 巻:51, 号:18, 開始ページ:2529, 終了ページ:2532, 2010年05月, [査読有り], [筆頭著者, 責任著者]
    Synthetic construction of fucosyl chitobiose [GlcNAc beta 1 -> 4(Fuc alpha 1 -> 3)GlcNAc] as an allergy-associated carbohydrate epitope was accomplished from three building blocks. The trisaccharidic unit was further transformed into a carbohydrate monomer and polymerization of the glycomonomer proceeded smoothly to provide a series of glycopolymers having various carbohydrate densities. In addition to the organic syntheses, biological evaluations of the glycomonomer and the polymers were carried out and sugar-clustering effects were observed. (C) 2010 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tetlet.2010.03.004
    DOI ID:10.1016/j.tetlet.2010.03.004, ISSN:0040-4039, ORCID:41457012, Web of Science ID:WOS:000276972200039
  • Simple and conveniently accessible bi-fluorescence-labeled substrates for amylases               
    Hiroyuki Oka; Tetsuo Koyama; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 巻:20, 号:6, 開始ページ:1969, 終了ページ:1971, 2010年03月, [査読有り], [最終著者, 責任著者]
    Synthesis of bi-fluorescence-labeled maltooligosaccharides for amylase assay was accomplished. Preliminary biological evaluation of both bi-fluorescence-labeled maltohexasaccharide and maltose using alpha-amylase was carried out, and the hexaosyl derivative showed unique variation on the basis of fluorescence resonance energy transfer (FRET). (C) 2010 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmcl.2010.01.117
    DOI ID:10.1016/j.bmcl.2010.01.117, ISSN:0960-894X, ORCID:41457010, Web of Science ID:WOS:000275221500038
  • Analytical investigations of the behavior of silole-core dendrimers with peripheral globotriaose in water and acetone/water mixed solvent               
    Hiroaki Aizawa; Ken Hatano; Hitoshi Saeki; Nobuaki Honsho; Tetsuo Koyama; Koji Matsuoka; Daiyo Terunuma
    TETRAHEDRON LETTERS, 巻:51, 号:12, 開始ページ:1545, 終了ページ:1549, 2010年03月, [査読有り]
    A new compound having a 2,3,4,5-tetraphenylsilole derivative on the center silicon of Dumbbell(1)6Gb3; Silole-Dumbbell(1)6Gb3 (1) was previously reported. It was found that 1 exhibited strongly increased fluorescence both in water and in a 96% acetone/water mixed solvent. The physical behavior of 1 in water and in the 96% acetone/water mixed solvent was investigated, and analyses including fluorescence quantum yields, dynamic-light-scattering (DLS), atomic-force-microscopy (AFM), and fluorescence microscopy were carried Out. It was clarified that I dynamically formed different types of aggregates in water and in higher acetone concentrations to yield high aggregation-induced emission (AIE) effects due to the formation of micelle-like particles in water and inversion-type micelles in the acetone/water mixed solvent, respectively. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tetlet.2010.01.041
    DOI ID:10.1016/j.tetlet.2010.01.041, ISSN:0040-4039, ORCID:41457009, Web of Science ID:WOS:000275552000004
  • Bifunctional cytosolic UDP-glucose 4-epimerases catalyse the interconversion between UDP-D-xylose and UDP-L-arabinose in plants               
    Toshihisa Kotake; Ryohei Takata; Rajeev Verma; Masato Takaba; Daisuke Yamaguchi; Takahiro Orita; Satoshi Kaneko; Koji Matsuoka; Tetsuo Koyama; Wolf-Dieter Reiter; Yoichi Tsumuraya
    BIOCHEMICAL JOURNAL, 巻:424, 開始ページ:169, 終了ページ:177, 2009年12月, [査読有り]
    UDP-sugars serve as substrates in the synthesis of cell wall polysaccharides and are themselves generated through sequential interconversion reactions from UDP-G1c (UDP-glucose) as the starting substrate in the cytosol and the Golgi apparatus. For the present study, a soluble enzyme with UDP-Xyl (UDP-xylose) 4-epimerase activity was purified approx. 300-fold from pea (Pisum sativum L.) sprouts by conventional chromatography. The N-terminal amino acid sequence of the enzyme revealed that it is encoded by a predicted UDP-Glc 4-epimerase gene, PsUGE1, and is distinct from the UDP-Xyl 4-epimerase localized in the Golgi apparatus. rPsUGE1 (recombinant P. sativum UGE1) expressed in Escherichia coli exhibited both UDP-Xyl 4-epimerase and UDP-Glc 4-epimerase activities with apparent K-m values of 0.31, 0.29,0.16 and 0.15 mM for UDP-Glc, UDP-Gal (UDP-galactose), UDP-Ara (UDP-L-arabinose) and UDP-Xyl respectively. The apparent equilibrium constant for UDP-Ara formation front UDP-Xyl was 0.89, whereas that for UDP-Gal formation from UDP-Glc was 0.24. Phylogenetic analysis revealed that PsUGE1 forms a group with Arabidopsis UDP-Glc 4-epimerases, AtUGE1 and AtUGE3, apart from a group including AtUGE2, AtUGE4 and AtUGE5. Similar to rPsUGE1, recombinant AtUGE1 and AtUGE3 expressed in E. coli showed high UDP-Xyl 4-epimerase activity in addition to their UDP-Glc 4-epimerase activity. Our results suggest that PsUGE1 and its close homologues catalyse the interconversion between UDP-Xyl and UDP-Ara as the last step in the cytosolic de novo pathway For UDP-Ara generation. Alternatively, the net flux of metabolites may be from UDP-Ara to UDP-Xyl as part of the salvage pathway for Ara.
    PORTLAND PRESS LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1042/BJ20091025
    DOI ID:10.1042/BJ20091025, ISSN:0264-6021, eISSN:1470-8728, ORCID:41457013, Web of Science ID:WOS:000272135100002
  • Relapsing fever Borrelia binds to neolacto glycans and mediates rosetting of human erythrocytes               
    Betty P. Guo; Susann Teneberg; Robert Munch; Daiyo Terunuma; Ken Hatano; Koji Matsuoka; Jonas Angstrom; Thomas Boren; Sven Bergstrom
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 巻:106, 号:46, 開始ページ:19280, 終了ページ:19285, 2009年11月, [査読有り]
    A hallmark of acute relapsing fever borreliosis is severe bacteremia. Some Borrelia species, such as B. duttonii and B. crocidurae, associate with erythrocytes and induce aggregation recognized as erythrocyte rosetting. Erythrocyte rosettes contribute to disease severity by increased tissue invasiveness (such as invasion of CNS and encephalitis), hemorrhaging, and reduced blood flow in affected microcapillaries. Here we report that relapsing fever Borrelia binds to neolacto (Gal beta 4GlcNAc beta 3Gal beta 4Glc beta 1)-carrying glycoconjugates that are present on human erythrocytes. This interaction is of low affinity but is compensated for by the multivalency of neo-lacto-oligosaccharides on the erythrocyte cell surface. Hence, the protein-carbohydrate interaction is dependent on multivalent neolacto-glycans to mediate binding.
    NATL ACAD SCIENCES, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1073/pnas.0905470106
    DOI ID:10.1073/pnas.0905470106, ISSN:0027-8424, ORCID:41457015, Web of Science ID:WOS:000271907400013
  • Fluorescence quenching detection of peanut agglutinin based on photoluminescent silole-core carbosilane dendrimer peripherally functionalized with lactose               
    Ken Hatano; Hitoshi Saeki; Hiroo Yokota; Hiroaki Aizawa; Tetsuo Koyama; Koji Matsuoka; Daiyo Terunuma
    TETRAHEDRON LETTERS, 巻:50, 号:42, 開始ページ:5816, 終了ページ:5819, 2009年10月, [査読有り]
    A glycocluster peripherally functionalized with a lactose (Lac: Gal beta 1 -> 4Glc beta 1-) derivative possessing a silole moiety as a luminophore was synthesized. The photoluminescence spectrum of the glycocluster showed extremely strong emission at 474 nm and the absolute quantum yield was estimated to be 92% in distilled water. The emission intensity was decreased by increasing the amount of peanut agglutinin (PNA), a lactose-binding lectin, and plots of the relative fluorescence intensity revealed a decline of 95% in emission intensity. Fluorescence quenching of the glycocluster upon mixing with PNA could be easily observed by the naked eye under UV irradiation, whereas no distinct change in fluorescence properties of the glycocluster was observed when wheat germ agglutinin (WGA) was employed. (C) 2009 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tetlet.2009.07.153
    DOI ID:10.1016/j.tetlet.2009.07.153, ISSN:0040-4039, ORCID:41457014, Web of Science ID:WOS:000269967500013
  • Synthesis of sialic acid derivatives having a C = C double bond substituted at the C-5 position and their glycopolymers               
    Kaori Suzuki; Jun-Ichi Sakamoto; Tetsuo Koyama; Sangchai Yingsakmongkon; Yasuo Suzuki; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 巻:19, 号:17, 開始ページ:5105, 終了ページ:5108, 2009年09月, [査読有り], [最終著者, 責任著者]
    Glycomonomers of sialic acid in which the acetamide group at C-5 was converted into two kinds of C = C double bond substituents were prepared and the fully protected glycomonomers were directly polymerized before deprotection steps. Radical polymerization with acrylamide in DMF in the presence of ammonium persulfate and N,N,N',N'-tetramethylethylenediamine proceeded smoothly and gave corresponding sialopolymers. Interestingly glycomonomers had hemagglutination inhibitory activities not only for H1N1 but also for H3N2 of human influenza virus strains. (C) 2009 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmcl.2009.07.034
    DOI ID:10.1016/j.bmcl.2009.07.034, ISSN:0960-894X, ORCID:41457018, Web of Science ID:WOS:000268863800048
  • Systematic syntheses of influenza neuraminidase inhibitors: A series of carbosilane dendrimers uniformly functionalized with thioglycoside-type sialic acid moieties               
    Jun-Ichi Sakamoto; Tetsuo Koyama; Daisei Miyamoto; Sangchai Yingsakmongkon; Kazuya I. P. J. Hidari; Wipawee Jampangern; Takashi Suzuki; Yasuo Suzuki; Yasuaki Esumi; Takemichi Nakamura; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
    BIOORGANIC & MEDICINAL CHEMISTRY, 巻:17, 号:15, 開始ページ:5451, 終了ページ:5464, 2009年08月, [査読有り], [最終著者, 責任著者]
    In order to develop novel influenza sialidase inhibitors, we constructed a library of glycoclusters composed of twelve types of sialylated dendrimers with thioglycosidic linkage that are resistant to hydrolysis by the sialidases. These sialodendrimers were synthesized by condensation reaction between a thiosialoside modified on the aglycon terminal end by a thioacetyl group and twelve types of carbosilane dendrimers having brominated terminal ends under deacetylation conditions, and temporal re-protection was performed for purification. Removal of all protection of the glycodendrimers was accomplished by transesterification and subsequent saponification to provide corresponding water-soluble glycodendrimers in good yields. For investigation of the structure-activity relationship, dendrimer scaffolds having differences in number of the sugar moieties, such as 3-, 4-, 6-and 12-functionalized dendrimers, and in linkage patterns, such as normal aliphatic linkage, ether-and amide-linkages. Biological evaluations of these glycodendrimers showed that all of the ether-and amide-elongated compounds had inhibitory potencies for the influenza sialidases in the mM range, while compounds having normal aliphatic linkage did not have any activities except for a 12-functionalized compound. (C) 2009 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmc.2009.06.036
    DOI ID:10.1016/j.bmc.2009.06.036, ISSN:0968-0896, eISSN:1464-3391, ORCID:41457020, Web of Science ID:WOS:000268099700012
  • Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl α(2-3) lactose moieties as inhibitors for human influenza viruses               
    Hiroyuki Oka; Tomotsune Onaga; Tetsuo Koyama; Chao-Tan Guo; Yasuo Suzuki; Yasuaki Esumi; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
    BIOORGANIC & MEDICINAL CHEMISTRY, 巻:17, 号:15, 開始ページ:5465, 終了ページ:5475, 2009年08月, [査読有り], [最終著者, 責任著者]
    A series of carbosilane dendrimers uniformly functionalized with sialyl lactose moieties (Neu5Ac alpha 2 -> 3-Gal beta 1 -> 4Glc) was systematically synthesized, and biological evaluations for anti-influenza virus activity using the glycodendrimers were performed. The results suggested that the glycodendrimers had unique biological activities depending on the form of their core frame, and Dumbbell(1)6-amide type glycoden-drimer 7 showed particularly strong inhibitory activities against human influenza viruses [A/PR/8/34 (H1N1) and A/Aichi/2/68 (H3N2)]. The results suggested that the structure-activity relationship (SAR) on the glycolibrary against various influenza viruses was observed, and dumbbell-shaped dendrimers as supporting carbohydrate moieties were found to be the most suitable core scaffolds in this study. (C) 2009 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmc.2009.06.035
    DOI ID:10.1016/j.bmc.2009.06.035, ISSN:0968-0896, ORCID:41457016, Web of Science ID:WOS:000268099700013
  • Synthesis and Characterization of Photo-Responsive Carbosilane Dendrimers               
    Tetsuo Koyama; Ken Hatano; Koji Matsuoka; Yasuaki Esumi; Daiyo Terunuma
    MOLECULES, 巻:14, 号:6, 開始ページ:2226, 終了ページ:2234, 2009年06月, [査読有り]
    Preparation of photo-responsive carbosilane dendrimers bearing 4-phenylazobenzonitrile units on their molecular surface has been accomplished, and their both photo and thermal behaviors have also been characterized. These functional dendrimers suggest that the apparent molecular sizes of the cis-isomers are smaller than those of the corresponding trans-isomers, since the molecular diameter of these dendrimers would be shorter on the basis of trans -> cis photo-isomerization of azobenzene.
    MOLECULAR DIVERSITY PRESERVATION INTERNATIONAL-MDPI, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.3390/molecules14062226
    DOI ID:10.3390/molecules14062226, ISSN:1420-3049, Web of Science ID:WOS:000267339500024
  • Synthetic construction of a Le(x) determinant via gabriel amine synthesis and the glycopolymer involving highly clustered Le(x) residues               
    Koji Matsuoka; Tatsuya Kohzu; Takashi Hakumura; Tetsuo Koyama; Ken Hatano; Daiyo Terunuma
    TETRAHEDRON LETTERS, 巻:50, 号:21, 開始ページ:2593, 終了ページ:2596, 2009年05月, [査読有り], [筆頭著者, 責任著者]
    Synthetic construction of a Le(x) determinant was accomplished via slightly modified Gabriel amine synthesis from three building blocks. Further transformations followed by polymerization of the Le(x) derivative gave a glycopolymer having trisaccharidic units as pendant-type epitopes. (C) 2009 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tetlet.2009.03.099
    DOI ID:10.1016/j.tetlet.2009.03.099, ISSN:0040-4039, CiNii Articles ID:80020274265, Web of Science ID:WOS:000265731300040
  • Use of a recycle-type SEC method as a powerful tool for purification of thiosialoside derivatives               
    Jun-Ichi Sakamoto; Chiharu Takita; Tetsuo Koyama; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
    CARBOHYDRATE RESEARCH, 巻:343, 号:16, 開始ページ:2735, 終了ページ:2739, 2008年11月, [査読有り], [最終著者, 責任著者]
    An efficient separation between fully acetylated thiosialoside methyl esters and fully acetylated Neu5A-c2en methyl esters was accomplished by means of a size-exclusion chromatography (SEC) method. Purity determinations and structural elucidation of the isolated compounds were performed by a combination of elemental analyses and spectroscopic analyses, including IR, (1)H, and (13)C NMR, and mass spectroscopic analyses. (C) 2008 Elsevier Ltd. All rights reserved.
    ELSEVIER SCI LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.carres.2008.05.014
    DOI ID:10.1016/j.carres.2008.05.014, ISSN:0008-6215, CiNii Articles ID:80019881611, Web of Science ID:WOS:000260735900003
  • Synthesis and lectin-binding activity of luminescent silica particles peripherally functionalized with lactose               
    Ken Hatano; Tetsuya Yamazaki; Koji Yoshino; Naoto Ohyama; Tetsuo Koyama; Koji Matsuoka; Daiyo Terunuma
    TETRAHEDRON LETTERS, 巻:49, 号:39, 開始ページ:5593, 終了ページ:5596, 2008年09月, [査読有り]
    A novel O-protected lactose (Gal beta 1 -> 4Glc beta 1-) derivative bearing trimethoxysilyl group at the aglycon was developed as a silane coupling agent. Reaction of the coupling agent with tris(2,2'-bipyridine)ruthenium (II) dlichloride (Rubpy) doped silica particle gave a Rubpy-doped silica particle peripherally functionalized with O-protected lactose derivative. De-O-protection of the particle with aqueous ammonia provided lactose-coating Rubpy-doped silica particles, combining luminophor encapsulated in silica matrix and carbohydrate having lectin-recognition ability. Specific adhesion of fluorescein isothiocyanate-labeled peanut agglutinin (FITC-PNA) to the lactose-coating Rubpy-doped silica particles was confirmed by fluorescence microscopic analysis. (C) 2008 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tetlet.2008.07.034
    DOI ID:10.1016/j.tetlet.2008.07.034, ISSN:0040-4039, CiNii Articles ID:80019747433, Web of Science ID:WOS:000259309700008
  • Sialyl α(2-3) lactose clusters using carbosilane dendrimer core scaffolds as influenza hemagglutinin blockers               
    Hiroyuki Oka; Tomotsune Onaga; Tetsuo Koyama; Chao-Tan Guo; Yasuo Suzuki; Yasuaki Esumi; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 巻:18, 号:15, 開始ページ:4405, 終了ページ:4408, 2008年08月, [査読有り], [最終著者, 責任著者]
    An efficient synthesis of a series of carbosilane dendrimers uniformly functionalized with sialyl alpha(2 -> 3) lactose (Neu5Ac alpha(2 -> 3)Gal beta(1 -> 4)Glc beta 1 ->) moieties was accomplished. The results of a preliminary study on biological responses against influenza virus hemagglutinin, using the sialyl lactose clusters showed unique biological activities on the basis of the structure-activity relationship according to the carbosilane scaffolds. (c) 2008 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmcl.2008.06.101
    DOI ID:10.1016/j.bmcl.2008.06.101, ISSN:0960-894X, PubMed ID:18639456, Web of Science ID:WOS:000257986400034
  • Properties of family 79 beta-glucuronidases that hydrolyze beta-glucuronosyl and 4-O-methyl-beta-glucuronosyl residues of arabinogalactan-protein               
    Tomoyuki Konishi; Toshihisa Kotake; Dina Soraya; Koji Matsuoka; Tetsuo Koyama; Satoshi Kaneko; Kiyohiko Igarashi; Masahiro Samejima; Yoichi Tsumuraya
    CARBOHYDRATE RESEARCH, 巻:343, 号:7, 開始ページ:1191, 終了ページ:1201, 2008年05月, [査読有り]
    The carbohydrate moieties of arabinogalactan-proteins (AGPs), which are mainly composed of Gal, L-Ara, GlcA, and 4Me-GlcA residues, are essential for the physiological functions of these proteoglycans in higher plants. For this study, we have identified two genes encoding family 79 beta-glueuronidases, designated AnGlcAase and NcGlcAase, in Aspergillus niger and Neurospora crassa, respectively, based on the amino acid sequence of a native beta-glucuronidase purified from a commercial pectolytic enzyme preparation from A. niger. Although the deduced protein sequences of AnGlcAase and NcGlcAase were highly similar, the recombinant enzymes expressed in Pichia pastoris exhibited distinct substrate specificity toward 4-Me-GlcA residues of AGPs: recombinant ADGlcAase (rAnGlcAase) substantially liberated both GlcA and 4-Me-GlcA residues from radish AGPs, whereas recombinant NcGlcAase (rNcGlcAase) activity on the 4-Me-GlcA residues of AGPs was very low. Maximum activity of rAnGlcAase hydrolyzing PNP beta-GlcA occurred at pH 3.0-4.0, whereas the maximum rNcGlcAase activity was at pH 6.0. The apparent K. values of rAnGlcAase were 30.4 mu M for PNP beta-GlcA and 422 mu M for beta-GIcA-(1 -> 6)-Gal, and those of rNcGlcAase were 38.3 mu M and 378 mu M, respectively. Similar to the native enzyme, rAnGlcAase was able to catalyze the transglycosylation of GlcA residues from PNP beta-GlcA to various monosaccharide acceptors such as Glc, Gal, and Xyl. We propose that both AnGlcAase and NcGlcAase are instances of a novel type of beta-glucuronidase with the capacity to hydrolyze beta-GlcA and 4-Me-beta-GlcA residues of AGPs, although they differ significantly in their preferences. (c) 2008 Elsevier Ltd. All rights reserved.
    ELSEVIER SCI LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.carres.2008.03.004
    DOI ID:10.1016/j.carres.2008.03.004, ISSN:0008-6215, eISSN:1873-426X, CiNii Articles ID:80019465657, PubMed ID:18377882, Web of Science ID:WOS:000256004800007
  • A bifunctional enzyme with L-fucokinase and GDP-L-fucose pyrophosphorylase activities salvages free L-fucose in Arabidopsis               
    Toshihisa Kotake; Sachiko Hojo; Noriaki Tajima; Koji Matsuoka; Tetsuo Koyama; Yoichi Tsumuraya
    JOURNAL OF BIOLOGICAL CHEMISTRY, 巻:283, 号:13, 開始ページ:8125, 終了ページ:8135, 2008年03月, [査読有り]
    Monomeric sugars generated during the metabolism of polysaccharides, glycoproteins, and glycolipids are imported to the cytoplasm and converted to respective nucleotide sugars via monosaccharide 1-phosphates, to be reutilized as activated sugars. Because L-fucose (L-Fuc) is activated mainly in the form of GDP derivatives in seed plants, the salvage reactions for L-Fuc are expected to be independent from those for Glc, Gal, L-arabinose, and glucuronic acid, which are activated as UDP-sugars. For this study we have identified, in the genomic data base of Arabidopsis, the gene (designated AtFKGP) of a bifunctional enzyme with similarity to both L-fucokinase and GDP-L-Fuc pyrophosphorylase. Recombinant AtFKGP (rAt-FKGP) expressed in Escherichia coli showed both L-fucokinase and GDP-L-Fuc pyrophosphorylase activities, generating GDP-L-Fuc from L-Fuc, ATP, and GTPas the starting substrates. Point mutations in rAtFKGPs at either Gly(133) or Gly(830) caused loss of GDP-L-Fuc pyrophosphorylase and L-fucokinase activity, respectively. The apparent Km values of L-fucokinase activity of rAtFKGP for L-Fuc and ATP were 1.0 and 0.45mM, respectively, and those of GDP-L-Fuc pyrophosphorylase activity for L-Fuc 1-phosphate and GTP were 0.052 and 0.17mM, respectively. The expression of AtFKGP was detected in most cell types of Arabidopsis, indicating that salvage reactions for free L-Fuc catalyzed by AtFKGP occur ubiquitously in Arabidopsis. Loss-of-function mutants with tDNA insertion in AtFKGP exhibited higher accumulation of free L-Fuc in the soluble fraction than the wild-type plant. These results indicate that AtFKGP is a bifunctional enzyme with L-fucokinase and GDP-L-Fuc pyrophosphorylase activities, which salvages free L-Fuc in Arabidopsis.
    AMER SOC BIOCHEMISTRY MOLECULAR BIOLOGY INC, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1074/jbc.M710078200
    DOI ID:10.1074/jbc.M710078200, ISSN:0021-9258, eISSN:1083-351X, CiNii Articles ID:80019462702, PubMed ID:18199744, Web of Science ID:WOS:000254288000009
  • Site-specific, covalent attachment of Poly(dT)-Modified peptides to solid surfaces for Microarrays               
    Naoki Kimura; Takashi Okegawa; Kiyokazu Yamazaki; Koji Matsuoka
    BIOCONJUGATE CHEMISTRY, 巻:18, 号:6, 開始ページ:1778, 終了ページ:1785, 2007年11月, [査読有り], [最終著者, 責任著者]
    The present study reported proof-of-principle for a kinase assay approach that can detect specific peptide phosphorylation events. The method involves attachment of peptides onto commercial aminosilane and polycarbodiimide-coated glass slides, using a newly developed DNattach linker system that consists of a poly(dT) tail (Nisshinbo Industries Inc.), followed by a detection step using fluorescently labeled antiphosphoamino acid antibodies. The linker-modified peptides are efficiently synthesized by Michael addition between maleimidomodified peptides and thiol-containing DNattach. Specific covalent immobilization of the modified peptides onto aminosilane and poly carbodiimide-coated slides is then achieved by short exposure to UV-light. Highly selective and quantitative recognition by standard antiphosphoamino acid antibodies (antiphosphotyrosine and antiphosphoGFAP) and kinases (c-Src and PKA) to the corresponding modified peptides on the microarray spots is demonstrated. Furthermore, we found that this immobilization method provides greater signal-to-noise ratio and better discrimination ability of phosphorylated amino acids than does the conventional immobilization technique. The phosphorylation pattern of target sequences, detected using fluorescently labeled antiphosphoamino acid antibodies, revealed that the linker system preference of the kinase is determined by its activity profile.
    AMER CHEMICAL SOC, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1021/bc070083
    DOI ID:10.1021/bc070083, ISSN:1043-1802, CiNii Articles ID:80018089290, PubMed ID:17953441, Web of Science ID:WOS:000251166400014
  • Novel linear polymers bearing thiosialosides as pendant-type epitopes for influenza neuraminidase inhibitors               
    Koji Matsuoka; Chiharu Takita; Tetsuo Koyama; Daisei Miyamoto; Sangchai Yingsakmongkon; Kazuya I. P. J. Hidari; Wipawee Jampangern; Takashi Suzuki; Yasuo Suzuki; Ken Hatano; Daiyo Terunuma
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 巻:17, 号:14, 開始ページ:3826, 終了ページ:3830, 2007年07月, [査読有り], [筆頭著者, 責任著者]
    A conventional synthesis of alpha-thioglycoside of sialic acid as a glycomonomer was accomplished. Radical copolymerization of the glycomonomer with vinyl acetate proceeded smoothly to afford a new class of glycopolymers having thiosialoside residues, in which all protection was removed by a combination of transesterification and saponification to provide a water-soluble thiosialoside cluster. The results of a preliminary study on biological responses against influenza virus neuraminidases using the thiosialoside polymer as a candidate for a neuraminidase inhibitor showed that the glycopolymer has potent inhibitory activity against the neuraminidases. (C) 2007 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmcl.2007.05.016
    DOI ID:10.1016/j.bmcl.2007.05.016, ISSN:0960-894X, PubMed ID:17524642, Web of Science ID:WOS:000248074600003
  • Practical synthesis of fully protected globotriaose and its glycopolymers               
    Koji Matsuoka; Yusuke Goshu; Yutaka Takezawa; Tomonori Mori; Jun-Ichi Sakamoto; Akihiro Yamada; Tomotsune Onaga; Tetsuo Koyama; Ken Hatano; Philip W. Snyder; Eric J. Toone; Daiyo Terunuma
    CARBOHYDRATE POLYMERS, 巻:69, 号:2, 開始ページ:326, 終了ページ:335, 2007年06月, [査読有り], [筆頭著者, 責任著者]
    Convenient and useful construction of a trisaccharide moiety of globotriaosyl ceramide was performed by means of modified Ogawa's protocol. In order to evaluate an efficiency of new class of glycopolymers, further chemical transformations of the trisaccharide were accomplished to afford a globotriaosyl carbohydrate monomer, and homopolymerization of the monomer by a general radical polymerization protocol gave a high-density glycopolymer in 84.3% yield after usual work-up procedures. In addition to the homopolymer, a copolymer composed of carbohydrate units and acrylamide units was also synthesized by the radical polymerization in 96.7% yield. (C) 2006 Elsevier Ltd. All rights reserved.
    ELSEVIER SCI LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.carbpol.2006.10.011
    DOI ID:10.1016/j.carbpol.2006.10.011, ISSN:0144-8617, CiNii Articles ID:80018527330, Web of Science ID:WOS:000246901000017
  • Highly luminescent glycocluster: silole-core carbosilane dendrimer having peripheral globotriaose               
    Ken Hatano; Hiroaki Aizawa; Hiroo Yokota; Akihiro Yamada; Yasuaki Esumi; Hiroyuki Koshino; Tetsuo Koyama; Koji Matsuoka; Daiyo Terunuma
    TETRAHEDRON LETTERS, 巻:48, 号:25, 開始ページ:4365, 終了ページ:4368, 2007年06月, [査読有り]
    A novel glycocluster periphery functionalized by globotriaose (Ga1 sigma 1-4Ga1 beta 1-4Gc beta 1- ) possessing a silole moiety as a luminophor was synthesized. The photoluminescence spectrum of the glycocluster in pure water showed extremely strong emission at 475 nm. Analogous intense emission of the silole dendrimer was also observed in a lower water fraction of water/acetone mixture. The water fraction of the silole dendrimer solution strongly affected the emission intensity; however, these luminescences were constantly detected at around 475 nm. (c) 2007 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tetlet.2007.04.100
    DOI ID:10.1016/j.tetlet.2007.04.100, ISSN:0040-4039, CiNii Articles ID:80018537073, Web of Science ID:WOS:000247278100012
  • Thiosialoside clusters using carbosilane dendrimer core scaffolds as a new class of influenza neuraminidase inhibitors               
    Jun-Ichi Sakamoto; Tetsuo Koyama; Daisei Miyamoto; Sangchai Yingsakmongkon; Kazuya I. P. J. Hidari; Wipawee Jampangern; Takashi Suzuki; Yasuo Suzuki; Yasuaki Esumi; Ken Hatano; Daiyo Terunuma; Koji Matsuoka
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 巻:17, 号:3, 開始ページ:717, 終了ページ:721, 2007年02月, [査読有り], [最終著者, 責任著者]
    An efficient synthesis of a series of carbosilane dendrimers uniformly functionalized with alpha-thioglycoside of sialic acid was accomplished. The results of a preliminary study on biological responses against influenza virus sialidases using thiosialoside clusters showed that some of the glycodendrimers have inhibitory potencies against the sialidases. (c) 2006 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmcl.2006.10.085
    DOI ID:10.1016/j.bmcl.2006.10.085, ISSN:0960-894X, PubMed ID:17095224, Web of Science ID:WOS:000244170700029
  • Lactotriaose-containing carbosilane dendrimers: Syntheses and lectin-binding activities               
    Akihiro Yamada; Ken Hatano; Tetsuo Koyama; Koji Matsuoka; Naonori Takahashi; Kazuya I. P. J. Hidari; Takashi Suzuki; Yasuo Suzuki; Daiyo Terunuma
    BIOORGANIC & MEDICINAL CHEMISTRY, 巻:15, 号:4, 開始ページ:1606, 終了ページ:1614, 2007年02月, [査読有り]
    Carbosilane dendrimers periphery-functionalized with lactotriaose (GlcNAc beta 1-3Gal beta l-4Glc) with valencies of three, four, six, and twelve were prepared for use in a lectin-binding assay. A lactotriaose derivative was prepared from D-glucosamine and D-lactose derivatives. The N-Troc-protected glucosamine glycosyl donor and 3'-O-unprotected lactose glycosyl acceptor were condensed in the presence of silver trifluoromethanesulfonate and methylsulfenyl bromide to provide corresponding trisaccharide with new beta-1-3 linkages in 92% yield. The protection group of the trisaccharide was transformed into an acetyl group. The 4-pentenyl glycoside was prepared from the acetate via glycosyl bromide. The alkene was converted into acetyl sulfide by addition of thioacetic acid under radical conditions. The lactotriaose unit was linked with carbosilane dendrimers to afford acelyl-protected glycodendrimers. De-O-acetylation of the dendrimers was carried out in the presence of sodium methoxide and then aq NaOH to give the desired lactotriaose clusters using a carbosilane dendrimer backbone. Their biological activities toward WGA were evaluated by fluorescence methods. The binding constants of free lactotriaose and trivalent, tetravalent, hexavalent, and dodecavalent glycodendrimers to WGA were determined to be 1.1 x 10(3), 4.4 x 10(4), 5.1 x 10(4), 2.8 x 10(6), and 1.3 x 10(6) M-1, respectively. The hexavalent glycodendrimer showed a 2500-fold larger binding effect than that of free lactotriaose. (c) 2006 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.bmc.2006.12.030
    DOI ID:10.1016/j.bmc.2006.12.030, ISSN:0968-0896, Web of Science ID:WOS:000243983800002
  • Carbosilane dendrimers bearing globotriaoses: Syntheses of globotrioasyl derivative and introduction into carbosilane dendrimers               
    Koji Matsuoka; Mikiko Terabatake; Atsushi Umino; Yasuaki Esumi; Ken Hatano; Daiyo Terunuma; Hiroyoshi Kuzuhara
    BIOMACROMOLECULES, 巻:7, 号:8, 開始ページ:2274, 終了ページ:2283, 2006年08月, [査読有り], [筆頭著者, 責任著者]
    As an application of a one-pot reaction involving Birch reduction and subsequent S(N)2 reaction in liquid ammonia, synthetic assembly of trisaccharidic moieties of globotriaosyl ceramide onto carbosilane dendrimers was accomplished using tris(3-bromopropyl) phenylsilane and tris[tris(3-bromopropyl)silylpropyl] phenylsilane as the core scaffolds. The common globotriaosyl derivative having benzylsulfide functionality at the terminal of the aglycon was efficiently prepared from D-galactose and D-lactose as starting materials. The glycosyl donor derived from galactose and the glycosyl acceptor derived from lactose were condensed in the presence of silver triflate as the best promoter to provide corresponding trisaccharide with newly formed alpha-1-4 linkages in 90% yield. Fully benzylated protection of the trisaccharide was deprotected under the Birch reduction condition followed by acetylation to give an acetate in which alkene was converted into benzyl sulfide by radical addition of alpha-toluenethiol in high yields. On the other hand, carbosilane dendrimers were prepared from appropriate chlorosilanes as starting materials by a combination of hydrosylation followed by alkenylation. The terminal C=C double bonds of the carbosilanes were converted into corresponding alcohols by means of the usual hydroboration reaction, and the alcohols underwent further chemical manipulation to give carbosilane dendrimers with peripheral bromine atoms.
    AMER CHEMICAL SOC, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1021/bm060368+
    DOI ID:10.1021/bm060368+, ISSN:1525-7797, CiNii Articles ID:80018973734, PubMed ID:16903671, Web of Science ID:WOS:000239723100005
  • Carbosilane dendrimers bearing globotriaoses: Construction of a series of carbosilane dendrimers bearing globotriaoses               
    Koji Matsuoka; Mikiko Terabatake; Yasuaki Esumi; Ken Hatano; Daiyo Terunuma; Hiroyoshi Kuzhuhara
    BIOMACROMOLECULES, 巻:7, 号:8, 開始ページ:2284, 終了ページ:2290, 2006年08月, [査読有り], [筆頭著者, 責任著者]
    To enhance biological activities on the basis of the sugar cluster effect, a series of carbosilane dendrimers as core scaffolds for the construction of glycodendrimers was systematically synthesized from appropriate chlorosilanes by a combination of alkenylation and hydrosylation reactions. Those carbosilane dendrimers having terminal C=C double bonds underwent general hydroboration reactions to give corresponding primary polyols. Further transformations of the alcohols were then performed by mesylation followed by a displacement with NaBr to provide corresponding dendrimers with 4 to 36 bromine atoms at each terminal end. Assembly of trisaccharide moieties of globotriaosyl ceramide using alkyl halide-type carbosilane dendrimers as the core frame was conducted in liquid ammonia by a one-pot reaction involving selective removal of a benzyl group under the Birch reduction condition and subsequent S(N)2 reaction to yield a series of carbosilane dendrimers having appropriate numbers of trisaccharide moieties. These dendrimers have unique shapes and adequate numbers of terminal trisaccharide moieties. Some of the dendrimers showed unique biological activity against Stxs, which were produced by pathogenic Escherichia coli O157:H7.
    AMER CHEMICAL SOC, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1021/bm0603692
    DOI ID:10.1021/bm0603692, ISSN:1525-7797, CiNii Articles ID:80018973735, PubMed ID:16903672, Web of Science ID:WOS:000239723100006
  • Syntheses and Vero toxin-binding activities of carbosilane dendrimers periphery-functionalized with galabiose               
    Akihiro Yamada; Ken Hatano; Koji Matsuoka; Tetsuo Koyama; Yasuaki Esumi; Hiroyuki Koshino; Kumiko Hino; Kiyotaka Nishikawa; Yasuhiro Natori; Daiyo Terunuma
    TETRAHEDRON, 巻:62, 号:21, 開始ページ:5074, 終了ページ:5083, 2006年05月, [査読有り]
    Carbosilane dendrimers bearing galabiose (Gal alpha 1-4Gal) with three, four, and six galabiose units at the periphery of the dendrimers were synthesized for use as artificial inhibitors against Shiga toxins (Stxs) produced by Escherichia coli O157:H7. The galabiose unit, prepared from penta-O-acetyl-beta-D-galactopyranose, was linked with carbosilane dendrimers of three shapes to afford acety I-protected glycodendrimers in good yields. De-O-acetylation of the clusters was carried out in the presence of NaOMe and then aq NaOH to give the desired three shapes of galabiose-coated carbosilane dendrimers. Their biological activities toward Stxs were evaluated by kinetic analysis, binding assays, and cytotoxic assays. (c) 2006 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tet.2006.03.042
    DOI ID:10.1016/j.tet.2006.03.042, ISSN:0040-4020, CiNii Articles ID:80019168007, Web of Science ID:WOS:000237485300006
  • Structural analysis of the interaction between Shiga toxin B subunits and linear polymers bearing clustered globotriose residues               
    M Watanabe; K Igai; K Matsuoka; A Miyagawa; T Watanabe; R Yanoshita; Y Samejima; D Terunuma; Y Natori; K Nishikawa
    INFECTION AND IMMUNITY, 巻:74, 号:3, 開始ページ:1984, 終了ページ:1988, 2006年03月, [査読有り]
    We previously developed linear polymers bearing clustered trisaccharides of globotriaosylceramide (Gb3) as orally applicable Shiga toxin (Stx) neutralizers. Here, using a Gb3 polymer with a short spacer tethering the trisaccharide to the core, we found that shortening the spacer length markedly reduced the binding affinity for Stx2 but not Stx1. Moreover, mutational analysis revealed that the essential binding sites of the terminal trisaccharides were completely different between Stx1 and Stx2. These results provide the molecular basis for the interaction between Stx B subunits and Gb3 polymers.
    AMER SOC MICROBIOLOGY, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1128/IAI.74.3.1984-1988.2006
    DOI ID:10.1128/IAI.74.3.1984-1988.2006, ISSN:0019-9567, CiNii Articles ID:30020833216, ORCID:41457045, PubMed ID:16495579, Web of Science ID:WOS:000235817500066
  • Syntheses of a series of lacto-N-neotetraose clusters using a carbosilane dendrimer scaffold               
    A Yamada; K Hatano; T Koyama; K Matsuoka; Y Esumi; D Terunuma
    CARBOHYDRATE RESEARCH, 巻:341, 号:4, 開始ページ:467, 終了ページ:473, 2006年03月, [査読有り]
    4-Pentenyl (2,3,4,6-tetra-O-acetyl-beta-(D)-galactopyranosyl)-(1 -> 4)-(3,6-di-O-acetyl-2-deoxy-2-phthalimido-beta-(D)-glucopyranosyl)-( 1 -> 3)-(2,6-di-O-benzoyl-beta-(D)-gatactopyranosyl)-(1 -> 4)-2,3,6-tri-O-benzoyl-beta-(D)-glucopyranoside (4) was synthesized by regio-selective glycosylation of 4-pentenyl (2,6,-di-O-benzoyl-beta-(D)-galactopyranosyl)-(1 -> 4)-2,3,6-tri-O-benzoyl-beta-(D)-glueopyranoside and (2,3,4,6-tetra-O-acetyl-beta-(D)-galactopyranosyl)-(1 -> 4)-3,6-di-O-acetyl-2-deoxy-2-phthalimido-beta-(D)-glucopyranosyl chloride. By conversion of the protecting groups followed by thioacetylation, 4 was transformed into the corresponding lacto-N-neotetraose derivative, 5-(acetylthio)pentenyl (2,3,4,6-tetra-O-acetyl-beta-(D)-galactopyranosyl)-(1 -> 4)-O-(3,6-di-O-acetyl-2-acetamido-2-deoxy-beta-(D)-glucopyranosyl)-(1 -> 3)-(2,4,6-di-O-acetyl-beta-(D)-galactopyranosyl)-(1 -> 4)-2,3,6-tri-O-acetyl-beta-(D)-glucopyranoside (6). The lacto-N-neotetraose derivative 6 was introduced into carbosilane dendrimer cores of three shapes, and three kinds of new carbosilane dendrimers peripherally functionalized by lacto-N-neotetraose were obtained. (c) 2005 Elsevier Ltd. All rights reserved.
    ELSEVIER SCI LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.carres.2005.11.037
    DOI ID:10.1016/j.carres.2005.11.037, ISSN:0008-6215, CiNii Articles ID:80019328422, PubMed ID:16386236, Web of Science ID:WOS:000235726600004
  • Identification and characterization of carbohydrate molecules in mammalian cells recognized by dengue virus type 2               
    C Aoki; KIPJ Hidari; S Itonori; A Yamada; N Takahashi; T Kasama; F Hasebe; MA Islam; K Hatano; K Matsuoka; T Taki; CT Guo; T Takahashi; Y Sakano; T Suzuki; D Miyamoto; M Sugita; D Terunuma; K Morita; Y Suzuki
    JOURNAL OF BIOCHEMISTRY, 巻:139, 号:3, 開始ページ:607, 終了ページ:614, 2006年03月, [査読有り]
    The interaction between cell surface receptors and the envelope glycoprotein (EGP) on the viral membrane surface is the initial step of Dengue virus infection. To understand the host range, tissue tropism, and virulence of this pathogen, it is critical to elucidate the molecular mechanisms of the interaction of EGP with receptor molecules. Here, using a TLC/virus-binding assay, we isolated and characterized a carbohydrate molecule on mammalian cell surfaces that is recognized by dengue virus type 2 (DEN2). Structural determination by immunochemical methods showed that the carbohydrate structure of the purified glycosphingolipid was neolactotetraosylceramide (nLc(4)Cer). This glycosphingolipid was expressed on the cell surface of susceptible cells, such as human erythroleukemia K562 and baby hamster kidney BHK-21. All serotypes of DEN viruses, DEN1 to DEN4, reacted with nLc(4)Cer, and the non-reducing terminal disaccharide residue Ga1 beta 1-4GlcNAc beta 1- was found to be a critical determinant for the binding of DEN2. Chemically synthesized derivatives carrying multiple carbohydrate residues of nLc(4), but not nLc(4) oligosaccharide, inhibited DEN2 infection of BHK-21 cells. These findings strongly suggested that multivalent nLc(4) oligosaccharide could act as a competitive inhibitor against the binding of DEN2 to the host cells.
    JAPANESE BIOCHEMICAL SOC, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1093/jb/mvj067
    DOI ID:10.1093/jb/mvj067, ISSN:0021-924X, CiNii Articles ID:10018847231, PubMed ID:16567427, Web of Science ID:WOS:000237355200033
  • グロボ三糖担持カルボシランデンドリマーの合成 -カルボシランデンドリマー構造がO157:H7が産生するベロ毒素の阻害活性に及ぼす効果- (Review)               
    照沼大陽; 松岡浩司; 幡野健
    有機合成化学協会誌, 巻:63, 号:7, 開始ページ:722, 終了ページ:727, 2005年07月, [査読有り]
    As a novel type of artificial multivalent receptor for verotoxins, eight pairs of carbosilane dendrimers carrying up to 36 units of trisaccharide moieties of globotriaosyl ceramide (Gal alpha 1-4 Gal beta 1-4 Glc beta 1-Cer) were prepared. The receptors (referred to as SUPER TWIG) were obtained in a generally applicable one-pot reaction by treating periphery functionalized carbosilane dendrimers with globotriaose derivative which has a thiobenzyl ether moiety as a precursor for generation of thiolate anion under Birch reduction conditions. Biological estimations of SUPER TWIGs for inhibition of Shiga toxin-producing Escherichia coli O157: H 7 showed unexpected magnitude depend on the structure of the carbosilane dendrimer used both in vitro and in vivo. It was found that the carbosilane dendrimer carrying six periphery units of trisaccharide moieties (referred to as Dumbbell (1) 6) is one of the most effective agent among the SUPER TWIGs we prepared so far.
    SOC SYNTHETIC ORGANIC CHEM JPN, 日本語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.5059/yukigoseikyokaishi.63.722
    DOI ID:10.5059/yukigoseikyokaishi.63.722, ISSN:0037-9980, CiNii Articles ID:10016587901, ORCID:41457049, SCOPUS ID:25144523070, Web of Science ID:WOS:000230525000005
  • Synthesis and characterization of new soluble Polydiphenylsilane derivatives               
    Toshiyuki Sato; Ken Hatano; Norihiko Kamata; Koji Matsuoka; Daiyo Terunuma
    Polymer Preprints, Japan, 巻:54, 号:1, 開始ページ:337, 2005年
    Four types of copolymer(3a, 3b, 3c, 3d) were newly synthesized by polycondensation of α, ω -dilithiopolysilane derived from decaphenylcyclopentasilane(2) with dichlorosilanes(3a, 3b, 3c) and dichlorodisilane(3d). The reaction of 2 with dichlorosilanes(3a, 3b, 3c) gave the corresponding polymers. But main-products were five- and six-membered cyclic oligosilanes due to intramolecular-cyclization of the intermediates. On the other hand, with dichlorodisilane(3d), the amount of liner polysilane increased because the seven-memberd cyclic oligosilane is more difficult to form than the five- or six-membered cyclic oligosilanes.
    日本語, 研究論文(国際会議プロシーディングス)
    SCOPUS ID:33645575319
  • Syntheses of new polysilanes bearing pendant liquid-crystalline molecules (II)               
    Hideki Takahashi; Ken Hatano; Yoshio Aoki; Koji Matsuoka; Norihiko Kamata; Daiyo Terunuma
    Polymer Preprints, Japan, 巻:54, 号:1, 開始ページ:443, 2005年
    Polysilanes with pendant liquid-crystalline molecules, which consist of a methylene spacer and cyclohexylphenyl moiety as a mesogen core, were synthesized. The polysilanes were quite soluble in organic solvents such as THF and chloroform. The polysilanes were characterized by IR, UV-vis, PL, and 1H-NMR. Phase transition of the obtained polymer a was indicative of Tg (= 122°C) and Tc (=132°C) by polarized optical microscope. While, phase transition of the obtained polymer b was not indicative of clear Tg and Tc.
    日本語, 研究論文(国際会議プロシーディングス)
    SCOPUS ID:33645572418
  • Synthesis of a useful lauryl thioglycoside of sialic acid and its application               
    K Matsuoka; T Onaga; T Mori; JI Sakamoto; T Koyama; N Sakairi; K Hatano; D Terunuma
    TETRAHEDRON LETTERS, 巻:45, 号:51, 開始ページ:9383, 終了ページ:9386, 2004年12月, [査読有り], [筆頭著者, 責任著者]
    An efficient synthesis of a useful thioglycosyl donor 2 was accomplished directly from known peracetylated sialic acid methvl ester and 1-dodecanethiol (lauryl mercaptan) in the presence of BF3-OEt2. The reactivities of the lauryl glycosides for glycosidation by means of TMSOTf as a convenient promoter were investigated, and the lauryl thioglycoside showed satisfactory activities. Further transformation of the lauryl glycoside was also attempted to give a 5-azide analogue 14 of the sialic acid, which was also reacted with a secondary alcohol in the presence of TMSOTf to give known glycoside 15 in high yield. (C) 2004 Elsevier Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.tetlet.2004.10.105
    DOI ID:10.1016/j.tetlet.2004.10.105, ISSN:0040-4039, CiNii Articles ID:80017025809, Web of Science ID:WOS:000225648700017
  • Synthesis of glycoconjugate polymer carrying globotriaose as artificial multivalent ligand for Shiga toxin-producing Escherichia coli O157 : H7               
    A Miyagawa; H Kurosawa; T Watanabe; T Koyama; D Terunuma; K Matsuoka
    CARBOHYDRATE POLYMERS, 巻:57, 号:4, 開始ページ:441, 終了ページ:450, 2004年09月, [査読有り], [最終著者, 責任著者]
    As an artificial ligand, a glycoconjugate, polymer carrying carbohydrate moiety of lactosyl ceramide or globotriaosyl ceramide (Gb(3)) was synthesized. Gb(3) is known as the receptor of Shiga toxin-producing Escherichia coli O157:H7. The preparation of the glycoconjugate, polymer initially involves the construction of the carbohydrate moiety of Gb(3) derivative which has n-pentenyl group as polymerizable group. In addition, the n-pentenyl group of the Gb(3) derivative was modified and different polymerizable groups such as acrylamide group were introduced at omega-position of the aglycon. Radical polymerization of the synthesized glycosyl monomers with or without acrylamide proceeded smoothly in water using ammonium persulfate and N, N, N', N'-tetramethylethylenediamine as usual initiator system and gave water-soluble glycoconjugate polymers having various polymer compositions. These polymers have the potential to neutralize Shiga toxin by reason of cluster effect and multivalency. (C) 2004 Elsevier Ltd. All rights reserved.
    ELSEVIER SCI LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/j.carbpol.2004.06.001
    DOI ID:10.1016/j.carbpol.2004.06.001, ISSN:0144-8617, CiNii Articles ID:120001370469, Web of Science ID:WOS:000223881700010
  • Oral therapeutic agents with highly clustered globotriose for treatment of Shiga toxigenic Escherichia coli infections               
    M Watanabe; K Matsuoka; E Kita; K Igai; N Higashi; A Miyagawa; T Watanabe; R Yanoshita; Y Samejima; D Terunuma; Y Natori; K Nishikawa
    JOURNAL OF INFECTIOUS DISEASES, 巻:189, 号:3, 開始ページ:360, 終了ページ:368, 2004年02月, [査読有り]
    Shiga toxin (Stx) is a major virulence factor in infection with Stx-producing Escherichia coli (STEC). We developed a series of linear polymers of acrylamide, each with a different density of trisaccharide of globotriaosylceramide (Gb(3)), which is a receptor for Stx, and identified Gb(3) polymers with highly clustered trisaccharides as Stx adsorbents functioning in the gut. The Gb(3) polymers specifically bound to both Stx1 and Stx2 with high affinity and markedly inhibited the cytotoxic activities of these toxins. Oral administration of the Gb(3) polymers protected mice after administration of a fatal dose of E. coli O157: H7, even when the polymers were administered after the infection had been established. In these mice, the serum level of Stx was markedly reduced and fatal brain damage was substantially suppressed, which suggests that the Gb(3) polymers entrap Stx in the gut and prevent its entrance into the circulation. These results indicate that the Gb(3) polymers can be used as oral therapeutic agents that function in the gut against STEC infections.
    UNIV CHICAGO PRESS, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1086/381124
    DOI ID:10.1086/381124, ISSN:0022-1899, Web of Science ID:WOS:000188467900002
  • Glyco-silicon functional materials. Part 6. Synthesis of a useful anomeric thioacetate of an N-acetyllactosamine derivative and its application               
    K Matsuoka; T Ohtawa; H Hinou; T Koyama; Y Esumi; SI Nishimura; K Hatano; D Terunuma
    TETRAHEDRON LETTERS, 巻:44, 号:18, 開始ページ:3617, 終了ページ:3620, 2003年04月, [査読有り], [筆頭著者, 責任著者]
    A novel anomeric beta-thioacetate of an N-acetyllactosamine derivative was efficiently synthesized in high yield from the known 2-azido glycosyl chloride using thioacetic acid as a convenient reagent. The synthesis involved not only an S,2 replacement of the chloride by a carbothiolate anion but also a reductive acetamidation of the azide group. Applications of the thioacetate for glycosidation were demonstrated to provide both O- and S-glycosides in high yields. Furthermore, both intermediates gave a new class of glycoclusters that included thioglycosidic linkages. (C) 2003 Elsevier Science Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/S0040-4039(03)00697-X
    DOI ID:10.1016/S0040-4039(03)00697-X, ISSN:0040-4039, ORCID:41457056, Web of Science ID:WOS:000182496400006
  • Preparation of new carbosilane dendrimers having terminal mesogens and investigation of their liquid crystal characteristics
    T Tsuchida; C Shimazaki; K Hatano; K Matsuoka; Y Aoki; H Nohira; Y Esumi; D Terunuma
    KOBUNSHI RONBUNSHU, 巻:60, 号:10, 開始ページ:561, 終了ページ:568, 2003年, [査読有り]
    Both of a series of new second generation carbosilane dendrimers having a different number of branches (Me(n)G 2-Mesogen, n=1, 2, 3) and a novel carbosilane dendrimer having an increased length of methylene chain from the core to the second generation (Gradient G 2-Mesogen) with terminal cyanobiphenyl mesogens were prepared. The characterization of the dendrimers was carried out by using differential scanning calorimetry (DSC) and optical polarizing microscopy. All the dendrimers showed smectic A phase. The ranges of the smectic A phase and the texture size of Me(n)G 2-Mesogen were increased with increasing the number of branches. The behavior of phase transition temperature and the texture size of Gradient G 2-Mesogen were similar to those of Me(n)G-2 Mesogen.
    SOC POLYMER SCIENCE JAPAN, 日本語, 研究論文(学術雑誌)
    ISSN:0386-2186, ORCID:41457057, Web of Science ID:WOS:000186308000006
  • E3 ubiquitin ligase that recognizes sugar chains               
    Y Yoshida; T Chiba; F Tokunaga; H Kawasaki; K Iwai; T Suzuki; Y Ito; K Matsuoka; M Yoshida; K Tanaka; T Tai
    NATURE, 巻:418, 号:6896, 開始ページ:438, 終了ページ:442, 2002年07月, [査読有り]
    N-glycosylation of proteins in the endoplasmic reticulum (ER) has a central role in protein quality control(1-3). Here we report that N-glycan serves as a signal for degradation by the Skp1-Cullin1-Fbx2-Roc1 (SCF(Fbx2)) ubiquitin ligase complex. The F-box protein Fbx2 (ref. 4) binds specifically to proteins attached to N-linked high-mannose oligosaccharides and subsequently contributes to ubiquitination of N-glycosylated proteins. Pre-integrin beta1 is a target of Fbx2; these two proteins interact in the cytosol after inhibition of the proteasome. In addition, expression of the mutant Fbx2DeltaF, which lacks the F-box domain that is essential for forming the SCF complex, appreciably blocks degradation of typical substrates of the ER-associated degradation pathway(5,6). Our results indicate that SCF(Fbx2) ubiquitinates N-glycosylated proteins that are translocated from the ER to the cytosol by the quality control mechanism.
    NATURE PUBLISHING GROUP, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1038/nature00890
    DOI ID:10.1038/nature00890, ISSN:0028-0836, CiNii Articles ID:10011472232, PubMed ID:12140560, Web of Science ID:WOS:000177009700043
  • A therapeutic agent with oriented carbohydrates for treatment of infections by Shiga toxin-producing Escherichia coli O157 : H7               
    K Nishikawa; K Matsuoka; E Kita; N Okabe; M Mizuguchi; K Hino; S Miyazawa; C Yamasaki; J Aoki; S Takashima; Y Yamakawa; M Nishijima; D Terunuma; H Kuzuhara; Y Natori
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 巻:99, 号:11, 開始ページ:7669, 終了ページ:7674, 2002年05月, [査読有り]
    Infection with Shiga toxin (Stx)-producing Escherichia colt O157:H7, which causes diarrhea and hemorrhagic colitis in humans, often results in fatal systemic complications, such as neurological damage and hemolytic-uremic syndrome. Because Stx circulating in the blood is a major causative factor of these complications, the development of a Stx neutralizer that functions in the circulation holds promise as a viable therapy. Here we developed a series of carbosilane dendrimers, in which trisaccharides of globotriaosyl ceramide, a receptor for Stx, were variously oriented at their termini (referred to as SUPER TWIG), and identified a SUPER TWIG with six trisaccharides as a Stx neutralizer functioning in the circulation. This SUPER TWIG specifically bound to Stx with high affinity (K-d = 1.1 x 10(-6) M) and inhibited the incorporation of the toxin into target cells. Intravenous administration of the SUPER TWIG along with Stx to mice substantially reduced the fatal brain damage and completely suppressed the lethal effect of Stx. Moreover, the SUPER TWIG protected mice from challenge with a fatal dose of E. coli O157:H7, even when administered after the establishment of the infection. The SUPER TWIG neutralized Stx in vivo by a mechanism in which the accumulation and immediate degradation of Stx by phagocytic macrophages present in the reticuloendothelial system were induced. Taken together, our findings indicate that this SUPER TWIG is therapeutic agent against infections by Stx-producing E. coli.
    NATL ACAD SCIENCES, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1073/pnas.112058999
    DOI ID:10.1073/pnas.112058999, ISSN:0027-8424, CiNii Articles ID:80015437099, PubMed ID:12032341, Web of Science ID:WOS:000175908600063
  • Improved solubility of beta-cyclodextrin inclusion complexes by using liquid ammonia as a solvent and the possibility of asymmetric reduction               
    K Matsuoka; H Takahashi; Y Saito; D Terunuma; H Kuzuhara
    CARBOHYDRATE POLYMERS, 巻:47, 号:4, 開始ページ:373, 終了ページ:376, 2002年03月, [査読有り], [筆頭著者, 責任著者]
    Dramatic improvement in the poor solubility of P-cyclodextrin (P-CD) and its inclusion complexes in water was achieved by using liquid ammonia (liq. NH3) instead of water as the solvent. Asymmetric NaBH4 reduction of the carbonyl groups of the inclusion complexes in liq. NH3 was examined in a homogeneous condition to give the corresponding alcohols with moderate chirality. (C) 2002 Elsevier Science Ltd. All rights reserved.
    ELSEVIER SCI LTD, 英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1016/S0144-8617(01)00189-8
    DOI ID:10.1016/S0144-8617(01)00189-8, ISSN:0144-8617, CiNii Articles ID:120001370575, Web of Science ID:WOS:000172896000009
  • An alternative route for the construction of carbosilane dendrimers uniformly functionalized with lactose or sialyllactose moieties
    K Matsuoka; H Oka; T Koyama; Y Esumi; D Terunuma
    TETRAHEDRON LETTERS, 巻:42, 号:19, 開始ページ:3327, 終了ページ:3330, 2001年05月, [査読有り], [筆頭著者, 責任著者]
    A new approach for the formation of an acetylthio linkage on aglycon by means of a radical addition of thioacetic acid into the C-C double bond of the aglycon was examined. An introduction of a carbohydrate moiety into carbosilane dendrimers was demonstrated using a one-pot coupling reaction in MeOH-DMF in the presence of NaOMe via removal of an acetyl group of the acetylthio linkage in the saccharide moieties, producing a thiolate anion and a nucleophilic replacement of the thiolate to dendric alkyl bromide to form carbosilane dendrimers uniformly bearing lactose or sialyllactose moieties through thioether linkages in high yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    ISSN:0040-4039, ORCID:41457061, Web of Science ID:WOS:000168404000022
  • Regioselective synthesis of methylated beta-cyclodextrins leaving hydroxy groups
    K Matsuoka; Y Shiraishi; D Terunuma; H Kuzuhara
    TETRAHEDRON LETTERS, 巻:42, 号:8, 開始ページ:1531, 終了ページ:1533, 2001年02月, [査読有り], [筆頭著者, 責任著者]
    A series of methylated beta -cyclodextrins (CDs) regioselectively leaving one or two hydroxy groups were prepared, and fluorescence spectroscopic measurements showed that they have unique binding characteristics against 2-p-toluidinylnaphthalene-6-sulfonate as a guest molecule in aqueous solution. (C) 2001 Elsevier Science Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    ISSN:0040-4039, ORCID:41457063, Web of Science ID:WOS:000167034500034
  • Introduction of monosaccharides having functional groups onto a carbosilane dendrimer: A broadly applicable one-pot reaction in liquid ammonia involving Birch reduction and subsequent SN2 reaction
    K Matsuoka; H Kurosawa; Y Esumi; D Terunuma; H Kuzuhara
    CARBOHYDRATE RESEARCH, 巻:329, 号:4, 開始ページ:765, 終了ページ:772, 2000年12月, [査読有り], [筆頭著者, 責任著者]
    Benzylthioalkyl glycosides of D-glucuronic acid, N-acetyl-D-glucosamine, and N-acetylneuraminic acid (common monosaccharide constituents of natural oligosaccharide chains) have been prepared as sulfide precursors for the carbohydrate coating of dendric carbosilane cores and used in a generally applicable one-pot reaction (Birch reduction in liquid ammonia and subsequent SN2 reaction) to generate a thioether linkage between the monosaccharide moieties and a carbosilane dendrimer. The dendrimers were uniformly functionalized with the monosaccharides in good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.
    ELSEVIER SCI LTD, 英語, 研究論文(学術雑誌)
    ISSN:0008-6215, ORCID:41457066, Web of Science ID:WOS:000165638600006
  • An improved preparation of N,N′-diacetylchitobiose by continuous enzymatic degradation of colloidal chitin using dialysis tubing as a convenient separator               
    Koji Matsuoka; Yoshiaki Matsuzawa; Kimio Kusano; Daiyo Terunuma; Hiroyoshi Kuzuhara
    Biomacromolecules, 巻:1, 号:4, 開始ページ:798, 終了ページ:800, 2000年12月, [査読有り], [筆頭著者, 責任著者]
    英語, 研究論文(学術雑誌)
    DOI:https://doi.org/10.1021/bm0055910
    DOI ID:10.1021/bm0055910, ISSN:1525-7797, PubMed ID:11710214, SCOPUS ID:0034570962
  • Synthetic assembly of beta-CD moieties using carbosilane dendrimer as the core frame
    K Matsuoka; Y Saito; D Terumura; H Kuzuhara
    KOBUNSHI RONBUNSHU, 巻:57, 号:10, 開始ページ:691, 終了ページ:695, 2000年, [査読有り], [筆頭著者, 責任著者]
    In order to assemble beta -CD moieties using a carbosilane dendrimer as the core frame, a carbosilane dendrimer having 12 bromine atoms at the terminal positions has been synthesized from tetrakis{[3-(hydroxyl) propyl]silylpropyl}silane as starting material. One-pot coupling reaction between the carbosilane dendrimer and mono-6-deoxy-benzylmercapto-beta -CD in liquid ammonia for Birch reduction and the subsequent S(N)2 reaction gave the carbosilane dendrimer carrying 12 beta -CD moieties as a mixture with three compounds carrying 11, 10, or 9 beta -CD moieties. The mixture formed an inclusion complex with 2-p-toluidinyl-naphthalene-6-sulfonate (TNS) in water having a ratio of [CD] : [TNS]=2 : 1.
    SOC POLYMER SCIENCE JAPAN, 日本語, 研究論文(学術雑誌)
    ISSN:0386-2186, ORCID:41457069, Web of Science ID:WOS:000165125500012
  • Synthesis of amphiphilic chitopentaose and chitoheptaose derivatives using a common disaccharidic synthon as the chain elongation unit
    H Hinou; A Umino; K Matsuoka; D Terunuma; S Takahashi; Y Esumi; H Kuzuhara
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 巻:73, 号:1, 開始ページ:163, 終了ページ:171, 2000年01月, [査読有り]
    With interest in clustering bioactive chitooligosaccharides, a pair of amphiphilic derivatives of around DP (degree of polymerization) 6, which has been considered to be the minimum molecular length for some kinds of bioactivity, was synthesized. Homologous derivatives of chitopentaose and chitoheptaose carrying tetradecanoyl and tetradecyloxy groups at the NH and C-1 of the reducing ends, respectively, were actually obtained using a 1,6-anhydro-2-azido-2-deoxy-beta-D-glucopyranose derivative as the terminal precursor and a chitobiose derivative as the elongation unit. Micelle formation of both derivatives was assumed from the results obtained by dye solubilization tests.
    CHEMICAL SOC JAPAN, 英語, 研究論文(学術雑誌)
    ISSN:0009-2673, eISSN:1348-0634, ORCID:41457068, Web of Science ID:WOS:000085355700020
  • Preparation and characterization of water-soluble polysilanes bearing chiral pendant ammonium moieties
    D Terunuma; K Nagumo; N Kamata; K Matsuoka; H Kuzuhara
    POLYMER JOURNAL, 巻:32, 号:2, 開始ページ:113, 終了ページ:117, 2000年, [査読有り]
    The preparation and characterization of new amphiphilic polysilanes containing chiral pendant ammonium groups are described. Polyalkylphenylsilanes (alkyl; C-1-C-8) (I) were prepared, and the Friedel-Crafts reaction of I was carried out to give p-chloromethylated polysilanes (II). II were treated with optically active amines such as N, N-dimethyl-alpha-methylbenzylamine (1), N, N-dimethylphenylalaninol (2), N, N-dimethyl-O-acethylphenylalaninol (3), N, N-dimethyl-iso-leucinol (4), N, N-dimethylleucinol (5) and N, N-dimethyl-1-phenylethanol (6) to give the corresponding amphiphilic polysilanes bearing chiral pendant ammonium moieties. All polymers prepared were soluble in water, ethanol and acetonitrile. The circular dichromic spectra (CD) of the polymers in ethanol showed that the polymer had a screw-sense main chain.
    SOC POLYMER SCIENCE JAPAN, 英語, 研究論文(学術雑誌)
    ISSN:0032-3896, ORCID:41457067, Web of Science ID:WOS:000086127200005
  • Synthesis and reactivity of a 5-azido analogue of neuraminic acid               
    Matsuoka, K.; Oka, H.; Terunuma, D.; Kuzuhara, H.
    Carbohydrate Letters, 巻:4, 号:2, 開始ページ:123, 終了ページ:130, 2000年, [査読有り], [筆頭著者, 責任著者]
    英語, 研究論文(学術雑誌)
    ORCID:53133679, SCOPUS ID:0034435383
  • Bi-fluorescence-labeled maltoheptaoside: Convenient substrate for continual assay of α-amylase               
    S. I. Nishimura; N. Kimura; K. Matsuoka; Yuan Chuan Lee
    Carbohydrate Letters, 巻:4, 号:2, 開始ページ:77, 終了ページ:84, 2000年, [査読有り]
    A new maltoheptaose derivative was prepared as a useful substrate for continual assay of α-amylase. The maltoheptaoside has thionaphtyl group as a fluorescent energy donor at the reducing end and dansyl group as an acceptor group at the non-reducing end. Excitation of the thionaphthyl group at 290 nm results in emission at 523 nm from the dansyl group, while the emission from the thionaphthyl group is quenched by the dansyl group. This fluorescence energy transfer is reduced by the hydrolytic action with α-amylase and a significant decrease in the dansyl emission concomitant with an increase in the thionaphthyl emission was observed. Usefulness of this substrate was demonstrated for sensitive and continuous assay of α-amylase from Aspergillus oryzae.
    英語, 研究論文(学術雑誌)
    ISSN:1073-5070, PubMed ID:11506161, SCOPUS ID:0034435678
  • Synthetic assembly of trisaccharide moieties of globotriaosyl ceramide using carbosilane dendrimers as cores. A new type of functional glyco-material
    K Matsuoka; M Terabatake; Y Esumi; D Terunuma; H Kuzuhara
    TETRAHEDRON LETTERS, 巻:40, 号:44, 開始ページ:7839, 終了ページ:7842, 1999年10月, [査読有り], [筆頭著者, 責任著者]
    As a novel type of artificial receptor for Vero toxins, three pairs of carbosilane dendrimers uniformly carrying 12, 6, and 3 units of trisaccharide moieties of globotriaosyl ceramide were prepared through formation of the sulfide linkages in liquid NH3, which revealed unexpected differences among their biological responses. (C) 1999 Elsevier Science Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    ISSN:0040-4039, ORCID:41457073, Web of Science ID:WOS:000083043400031
  • Preparation and characterization of novel carbosilane dendrimers carrying mesogens
    D Terunuma; T Kato; R Nishio; Y Aoki; H Nohira; K Matsuoka; H Kuzuhara
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 巻:72, 号:9, 開始ページ:2129, 終了ページ:2134, 1999年09月, [査読有り]
    A series of new carbosilane dendrimers carrying cyanobiphenyl derivatives was prepared starting from the tertiary core molecule, triallylphenylsilane. The phase transition of the dendrimers depends on the dendrimer generation, and the spacer lengths were investigated by using differential scanning calorimetry (DSC) and an optical polarizing microscope. All of the dendrimers prepared exhibited smectic A phases. The phase behavior on the phase-transition pattern of the DSC curve and the texture appearances of G2-mesogen(5) carrying twenty-seven mesogens were observed to be similar to that of the reported G2 dendrimer prepared starting from the quarternary core molecule, tetraallylsilane, carrying thirty-six mesogens.(4)
    CHEMICAL SOC JAPAN, 英語, 研究論文(学術雑誌)
    ISSN:0009-2673, eISSN:1348-0634, ORCID:41457072, Web of Science ID:WOS:000083033600025
  • Preparation and characterization of carbosilane dendrimers carrying mesogens with chiral substituent
    D Terunuma; R Nishio; Y Aoki; H Nohira; K Matsuoka; H Kuzuhara
    CHEMISTRY LETTERS, 号:7, 開始ページ:565, 終了ページ:566, 1999年07月, [査読有り]
    A series of new carbosilane dendrimers carrying a mesogenic group, 5-((+)-2-fluorooctyloxy) -2-phenylpyrimidine derivative, were prepared successfully. Although the dendrimers did not show any clear Sc* phases, it was found that all the dendrimers prepared were operative as chiral dopants.
    CHEMICAL SOC JAPAN, 英語, 研究論文(学術雑誌)
    ISSN:0366-7022, eISSN:1348-0715, ORCID:41457071, Web of Science ID:WOS:000081770000014
  • Novel synthesis of L-iduronic acid using trehalose as the disaccharidic starting material
    H Hinou; H Kurosawa; K Matsuoka; D Terunuma; H Kuzuhara
    TETRAHEDRON LETTERS, 巻:40, 号:8, 開始ページ:1501, 終了ページ:1504, 1999年02月, [査読有り]
    For the preparation of L-iduronic acid, trehalose was converted into a derivative of a novel disaccharide, beta-L-idopyranosyl beta-L-idopyranoside, through diastereoselective hydroboration of the 5, 5'-di-eno intermediate. The 6- and 6'-hydroxy groups were then oxidized in two steps to give a disaccharide composed of 2 units of L-iduronate moieties, which underwent acidic cleavage of the glycosidic bond to give the target compound. (C) 1999 Elsevier Science Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    ISSN:0040-4039, ORCID:41457070, Web of Science ID:WOS:000078513400021
  • Synthesis of carbosilane compounds functionalized with three or four beta-cyclodextrin moieties. Use of a one-pot reaction in liquid ammonia for birch reduction and the subsequent S(N)2 replacement
    K Matsuoka; M Terabatake; Y Saito; C Hagihara; Y Esumi; D Terunuma; H Kuzuhara
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 巻:71, 号:11, 開始ページ:2709, 終了ページ:2713, 1998年11月, [査読有り], [筆頭著者, 責任著者]
    As a basic model reaction for assembling specific functional carbohydrate molecules on a novel core substance by making covalent bonds, an efficient one-pot reaction involving Birch reduction and a subsequent S-N(2) replacement was developed, employing trivalent and tetravalent carbosilane bromides as the core and monodeoxy-monomercapto-beta-cyclodextrin as the functional carbohydrate. It was confirmed that carbosilane derivatives containing a suitable spacer molecule were of wide applicability as a new core substance for the construction of diverse functional materials.
    CHEMICAL SOC JAPAN, 英語, 研究論文(学術雑誌)
    ISSN:0009-2673, eISSN:1348-0634, ORCID:41457077, Web of Science ID:WOS:000077483400027
  • Synthetic conversion of cellobiose into the glycal-type monomers and their polymerization
    Y Ogawa; H Hinou; K Matsuoka; D Terunuma; H Kuzuhara
    TETRAHEDRON LETTERS, 巻:39, 号:32, 開始ページ:5789, 終了ページ:5792, 1998年08月, [査読有り]
    A pair of disaccharidic glycals thoroughly O-benzylated except the 4'- or the 6'-hydroxyl groups were prepared as the monomers for iodonium ion-promoted polymerization, which proceeded under dark conditions to give polysaccharides of more than DP 12 (24 saccharide). Reductive removal of the iodine atom and subsequent deprotection gave polysaccharides alternatively composed of beta-D-glucopyranosyl and 2-deoxy-alpha, beta-D-glucopyranosyl residues. (C) 1998 Elsevier Science Ltd. All rights reserved.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    ISSN:0040-4039, ORCID:41457078, Web of Science ID:WOS:000074905500033
  • Preparation of amphiphilic polysilanes bearing chiral pendant ammonium moieties
    D Terunuma; K Nagumo; N Kamata; K Matsuoka; H Kuzuhara
    CHEMISTRY LETTERS, 号:7, 開始ページ:681, 終了ページ:682, 1998年07月, [査読有り]
    The synthesis and characterization of new amphiphilic polysilanes containing chiral pendant ammonium groups are described. Chloromethylation of polyhexylphenylsilane (PHPS) was carried out to give p-chloromethylated PHPS (1). 1 was treated with optically active N,N-dimethyl- alpha -methylbenzylamine to give an amphiphilic polysilane. The polymer prepared was soluble in water, ethanol and acetonitrile. The circular dichromic spectrum of the polymer in ethanol showed that the the polymer had a screw-sense main chain.
    CHEMICAL SOC JAPAN, 英語, 研究論文(学術雑誌)
    ISSN:0366-7022, eISSN:1348-0715, ORCID:41457075, Web of Science ID:WOS:000075153700058
  • Preparation of new carbosilane dendrimers carrying mesogenic groups
    D Terunuma; T Kato; R Nishio; K Matsuoka; H Kuzuhara; Y Aoki; H Nohira
    CHEMISTRY LETTERS, 号:1, 開始ページ:59, 終了ページ:60, 1998年, [査読有り]
    A series of new carbosilane dendrimers was prepared by repeating a combination of hydrosilation and allylation on a core molecule, triallylphenylsilane. Subsequent hydroboration and oxidation of the dendrimers gave the polyol derivatives, which were treated with a mesogenic molecule, 6-(4-cyanobiphenyl-4-oxy)hexanoyl chloride, to give new carbosilane dendrimers carrying mesogenic groups. It was found that the all carbosilane dendrimers exhibited liquid crystal phases. The effects of the dendrimer generations on the ranges of liquid crystal temperatures were investigated.
    CHEMICAL SOC JAPAN, 英語, 研究論文(学術雑誌)
    ISSN:0366-7022, eISSN:1348-0715, ORCID:41457076, Web of Science ID:WOS:000072163200030
  • Efficient conversion of a 1,6-anhydro chitobiose derivative into the corresponding tetradecyl beta-glycoside derivative by means of participation of a neighboring tetradecanamide group
    A Umino; H Hinou; K Matsuoka; D Terunuma; S Takahashi; H Kuzuhara
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 巻:17, 号:2, 開始ページ:231, 終了ページ:239, 1998年, [査読有り]
    In the course of our studies on the synthesis of amphiphilic chitoheptaose derivatives carrying binary long hydrocarbon chains at the reducing sugar, tetradecyl 4-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-2-tetradecanamido-beta-D-glucopyranoside was prepared as a model. For general applicability, the 1,6-anhydro-2-deoxy-2-tetradecanamido-beta-D-glucopyranosyl moiety was employed as a precursor of the reducing end. Acetolysis of the 1,6-anhydro ring using triethylsilyl triflate gave an oxazoline intermediate as a major product, accompanied by alpha-glycosyl acetate as a by-product. Immediate treatment of the mixture with 1-tetradecanol and protic acid followed by a separation work-up efficiently led to tettadecyl beta-glycoside derivative.
    MARCEL DEKKER INC, 英語, 研究論文(学術雑誌)
    ISSN:0732-8303, ORCID:41457074, Web of Science ID:WOS:000072619200005
  • Synthesis of amphiphilic chitoheptaose derivative
    H Hinou; A Umino; K Matsuoka; D Terunuma; S Takahashi; Y Esumi; H Kuzuhara
    TETRAHEDRON LETTERS, 巻:38, 号:46, 開始ページ:8041, 終了ページ:8044, 1997年11月, [査読有り]
    With interest in clustering of bioactive chitooligosaccharides of more than dp 6, a chitoheptaose derivative 1 carrying tetradecanoyl and tetradecyloxy groups at the NH and the C-1 of the reducing end was prepared. The hydrophobic groups were introduced step by step after completion of the heptasaccharide skeleton using a chitobiose derivative as the elongation unit. Micelle formation of 1 in water was confirmed by dye solubilization check. (C) 1997 Elsevier Science Ltd.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    ISSN:0040-4039, ORCID:41457080, Web of Science ID:WOS:A1997YE89600025
  • Total synthesis of a heptasaccharide phytoalexine elicitor through solid phase synthesis
    K Matsuoka
    TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY, 巻:9, 号:49, 開始ページ:411, 終了ページ:412, 1997年09月, [査読有り], [筆頭著者, 責任著者]
    GAKUSHIN PUBL CO, 英語, 研究論文(学術雑誌)
    ISSN:0915-7352, ORCID:41457081, Web of Science ID:WOS:A1997YG02100005
  • Preparation of fluorescence-labeled neoglycolipids for ceramide glycanase assays
    K Matsuoka; SI Nishimura; YC Lee
    FLUORESCENCE SPECTROSCOPY, 巻:278, 開始ページ:519, 終了ページ:528, 1997年, [査読有り], [筆頭著者, 責任著者]
    ELSEVIER ACADEMIC PRESS INC, 英語
    ISSN:0076-6879, ORCID:41457079, Web of Science ID:WOS:A1997BJ03V00026
  • Chemical synthesis of cellulose
    K Matsuoka
    TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY, 巻:8, 号:44, 開始ページ:441, 終了ページ:442, 1996年11月, [査読有り], [筆頭著者, 責任著者]
    GAKUSHIN PUBL CO, 英語, 研究論文(学術雑誌)
    ISSN:0915-7352, ORCID:41457082, Web of Science ID:WOS:A1996WF78800008
  • A BI-FLUORESCENCE-LABELED SUBSTRATE FOR CERAMIDE GLYCANASE BASED ON FLUORESCENCE ENERGY-TRANSFER
    K MATSUOKA; SI NISHIMURA; YC LEE
    CARBOHYDRATE RESEARCH, 巻:276, 号:1, 開始ページ:31, 終了ページ:42, 1995年10月, [査読有り], [筆頭著者]
    An alkyl lactoside containing two different fluorescence probes as an energy donor and an energy acceptor was synthesized as a substrate for ceramide glycanase. n-Pentenyl beta-lactoside was converted into its 4',6'-O-(2-naphthylmethylidene) derivative with subsequent benzoylation of all remaining OH groups. The fully protected lactoside was treated with borane-trimethylamine complex and aluminum chloride in tetrahydrofuran [P.J. Garegg, Pure Appl. Chem., 56 (1984) 845-858] for selective opening of the 4',6'-acetal group to give the 6'-O-(2-naphthylmethyl) derivative in high yield, After O-debenzoylation, the omega-alkenyl group at the reducing end was extended by Michael addition with HS(CH2)(2)NH2 . HCl to provide an amino group at the terminal position. The amino group was then dansylated to give the target lactoside, which has two different fluorescent probes at each end, Excitation at 290 nm (of the 2-naphthyl group) of the bi-fluorescence-labeled lactoside showed emissions at 335 nm (2-naphthyl) and at 540 nm (dansyl). The distance between the naphthyl group and the dansyl group was estimated to be 12 Angstrom by the Forster relationship. Digestion of this lactoside with American leech (Macrobdella decora) ceramide glycanase [B. Zhou et al., J. Biol. Chem., 264 (1989) 12,272-12,277] resulted in an increase in the naphthyl emission with a concomitant decrease in the dansyl emission, These changes can be used for continuous monitoring of the ceramide glycanase activity.
    ELSEVIER SCIENCE BV, 英語, 研究論文(学術雑誌)
    ISSN:0008-6215, ORCID:41457083, Web of Science ID:WOS:A1995TC15600002
  • A NEW APPROACH TO ASSAY ENDO-TYPE CARBOHYDRASES - BIFLUORESCENT-LABELED SUBSTRATES FOR GLYCOAMIDASES AND CERAMIDE GLYCANASES
    KB LEE; K MATSUOKA; S NISHIMURA; YC LEE
    ANALYTICAL BIOCHEMISTRY, 巻:230, 号:1, 開始ページ:31, 終了ページ:36, 1995年09月, [査読有り]
    Glycoamidases and ceramide glycanases are important ''endo-type'' enzymes for structural elucidations of glycoconjugates as well as for construction of neoglycoconjugates. The assay methods currently available for these enzymes are tedious and do not permit continual assay of the enzyme activities. We modified a desialylated biantennary glycopeptide with 2-naphthylacetic acid at the N-terminus and at the nonreducing terminal galactosyl residues with mono-N-dansylethylenediamine, via a specific oxidation of the C-6 hydroxyl group with galactose oxidase. In such a substrate, the naphthyl fluorescence (lambda(em) = 335 nm) is quenched due to absorption of its emitted light by the dansyl group, which in turn results in emission of fluorescence (lambda(ex) = 520 nm) by the latter. However, when the link between the two fluorophores is severed by glycoamidase (PNGase), the energy transfer ceases to occur, Consequently the emission of the dansyl fluorescence and the quenching of naphthyl fluorescence diminish or disappear. Likewise, the energy transfer between the fluorophores in an alkyl lactoside containing a dansyl group at the terminal position of aglycon and a 2-naphthylmethyl group on the galactosyl residue is also eliminated by the glycosidic cleavage by a ceramide glycanase from American leech, Macrobdella decora, resulting in enhancement of the naphthyl emission and decrease in the dansyl emission. The substrates presented here permit continuous fluorescent monitoring of the enzymatic reaction. This allows precise analyses of enzyme kinetics not possible with the conventional assay methods for the endo-type enzymes which usually require separation of reaction products. (C) 1995 Academic Press, Inc.
    ACADEMIC PRESS INC JNL-COMP SUBSCRIPTIONS, 英語, 研究論文(学術雑誌)
    ISSN:0003-2697, ORCID:41457085, Web of Science ID:WOS:A1995RT93000006
  • GLYCOCONJUGATES .5. POLYMERIC SUGAR LIGANDS AVAILABLE FOR DETERMINING THE BINDING-SPECIFICITY OF LECTINS
    K MATSUOKA; SI NISHIMURA
    MACROMOLECULES, 巻:28, 号:8, 開始ページ:2961, 終了ページ:2968, 1995年04月, [査読有り], [筆頭著者]
    Systematic syntheses of polymerizable N-acetyllactosamine and related disaccharide derivatives have been accomplished by introducing an n-pentenyl group at each reducing end as a simple and versatile polymerizable aglycon. Radical copolymerizations of these sugar monomers with acrylamide proceeded smoothly in water by means of ammonium persulfate and N,N,N',N'-tetramethylethylenediamine as initiators and to give water-soluble glycopolymers in good yields. In addition to chemical syntheses of glycopolymers, chemoenzymic galactosylation of the polymeric GlcNAc ligand was also completely performed by means of bovine galactosyl transferase activity in the presence of uridine 5'-diphosphogalactose as a sugar donor. These glycopolymers were demonstrated to exhibit enhanced binding capacity with lectins on the basis of polymeric sugar-cluster effect. It was suggested that the polymeric LacNAc ligand showed much higher affinity to Erythrina corallodendron lectin than other polymers having positional LacNAc isomers from the inhibitory assay of hemagglutination by Erythrina corallodendron. The order of the inhibitory effects of these polymers on hemagglutination by Erythrina corallodendron was Gal beta(1-4)GlcNAc (LacNAc) >> Gal beta(1-4)Glc (Lac) >> Gal beta(1-3)GlcNAc > Gal beta(1-6)GlcNAc similar or equal to Gal.
    AMER CHEMICAL SOC, 英語, 研究論文(学術雑誌)
    ISSN:0024-9297, ORCID:41457117, Web of Science ID:WOS:A1995QT94600049
  • A FACILE AND QUANTITATIVE PREPARATION OF ACTIVATED CYCLIC SUGAR-DERIVATIVES USING HGBR2 AND 2,4,6-COLLIDINE
    K MATSUOKA; SI NISHIMURA; YC LEE
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 巻:68, 号:6, 開始ページ:1715, 終了ページ:1720, 1995年, [査読有り], [筆頭著者]
    A combination of mercury(II) bromide (HgBr2) and 2,4,6-collidine was found to promote the formation of activated cyclic sugar derivatives such as 1,2-orthoesters and an oxazoline derivative in quantitative yields at room temperature. A slightly hindered skew like conformation of the lactose orthoester derivative was revealed by H-1 NMR analysis. It was also suggested that the reaction of a lactose 1,2-orthoester with trimethylsilyl azide proceeded smoothly to give beta-lactosyl azide stereoselectively which is a useful intermediate for constructing glycopeptides and neoglycoconjugates.
    CHEMICAL SOC JAPAN, 英語, 研究論文(学術雑誌)
    ISSN:0009-2673, eISSN:1348-0634, ORCID:41457084, Web of Science ID:WOS:A1995RJ19400027
  • SYNTHESIS OF BI-FLUORESCENCE-LABELED LACTOSIDE - A SUBSTRATE FOR CONTINUAL ASSAY OF CERAMIDE GLYCANASE
    K MATSUOKA; SI NISHIMURA; YC LEE
    TETRAHEDRON-ASYMMETRY, 巻:5, 号:12, 開始ページ:2335, 終了ページ:2338, 1994年12月, [査読有り], [筆頭著者]
    A bi-fluorescence labeled derivative suitable for analysis of ceramide glycanase activity was constructed from 4-pentenyl lactoside. Selective modification of the galactosyl residue was attained by formation of 4',6'-naphthylmethylidene derivative, which was followed by regioselective reductive ring opening. The aglycon was extended by Michael addition of 2-aminoethanetiol, and dansylated at the terminal amino group. Excitation of the naphthyl group results in emission from the dansyl group, while the emission from the naphthyl group is quenched by the dansyl group. Upon digestion with ceramide glycanase, the energy transfer is severed and a decrease in the dansyl emission concommitant with an increase in the naphthyl emission was observed. This substrate was successfully used to analyze ceramide glycanase activity.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    ISSN:0957-4166, ORCID:41457123, Web of Science ID:WOS:A1994PX86700003
  • SYNTHETIC GLYCOCONJUGATES .4. USE OF OMEGA-(ACRYLAMIDO)ALKYL GLYCOSIDES FOR THE PREPARATION OF CLUSTER GLYCOPOLYMERS
    SI NISHIMURA; T FURUIKE; K MATSUOKA; K MARUYAMA; K NAGATA; K KURITA; N NISHI; S TOKURA
    MACROMOLECULES, 巻:27, 号:18, 開始ページ:4876, 終了ページ:4880, 1994年08月, [査読有り]
    A simple and efficient method for the syntheses of clustering-sugar homopolymers from omega-(acrylamido)alkyl glycosides of N-acetyl-beta-D-glucosamine (GlcpNAc) is described. Radical polymerization of the new glycosides proceeded smoothly in an aqueous solution in the presence of ammonium persulfate and N,N,N',N'-tetramethylethylenediamine and gave water-soluble homopolymers having high density sugar branches as a novel class of cluster glycosides. The apparent association constant of wheat germ agglutinin (WGA) with poly[3-(N-acryloylamino)propyl 2-acetamido-2-deoxy-beta-D-glucopyranoside] was determined by measuring the change in fluorescence intensity produced by various concentrations of polymeric ligand and found to be approximately 10(8) M(-1). Addition of the cluster type GlcpNAc polymer to WGA induced much greater enhancement of the fluorescence intensity and a significant blue shift of the fluorescence emission maximum of WGA than did addition of the low-density GlcpNAc polymer derived from n-pentenyl glycoside.
    AMER CHEMICAL SOC, 英語, 研究論文(学術雑誌)
    ISSN:0024-9297, ORCID:41457125, Web of Science ID:WOS:A1994PE83000004
  • CHEMOENZYMATIC OLIGOSACCHARIDE SYNTHESIS ON A SOLUBLE POLYMERIC CARRIER
    SI NISHIMURA; K MATSUOKA; YC LEE
    TETRAHEDRON LETTERS, 巻:35, 号:31, 開始ページ:5657, 終了ページ:5660, 1994年08月, [査読有り]
    A facile and efficient method for the chemical and enzymatic syntheses of oligosaccharides using a new type of soluble polymeric sugar acceptor substrate is described. The water soluble glycopolymers having N-acetyl-D-glucosamine (GlcNAc) branches derived from a p-substituted benzyl glycosides were galactosylated with bovine milk galactosyl transferase. The flexible GlcNAc branches of the polymer chains allow quantitative galactosylation and subsequent hydrogenolysis proceeded smoothly to release the desired N-acetyl-lactosamine from the polymer support in high yield.
    PERGAMON-ELSEVIER SCIENCE LTD, 英語, 研究論文(学術雑誌)
    ISSN:0040-4039, ORCID:41457118, Web of Science ID:WOS:A1994PA14200032
  • COMPARISON OF ACID HYDROLYTIC CONDITIONS FOR ASN-LINKED OLIGOSACCHARIDES
    JQ FAN; Y NAMIKI; K MATSUOKA; YC LEE
    ANALYTICAL BIOCHEMISTRY, 巻:219, 号:2, 開始ページ:375, 終了ページ:378, 1994年06月, [査読有り]
    ACADEMIC PRESS INC JNL-COMP SUBSCRIPTIONS, 英語
    ISSN:0003-2697, ORCID:41457120, Web of Science ID:WOS:A1994NN59000027
  • CHEMOENZYMIC PREPARATION OF A GLYCOCONJUGATE POLYMER HAVING A SIALYLOLIGOSACCHARIDE - NEU5AC-ALPHA(2-]3)GAL-BETA(1-]4)GLCNAC
    SI NISHIMURA; KB LEE; K MATSUOKA; YC LEE
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 巻:199, 号:1, 開始ページ:249, 終了ページ:254, 1994年02月, [査読有り]
    Water-soluble polyacrylamide having 3'-sialyl N-acetyl-lactosamine [Neu5Ac alpha(2->3)Gal beta(1->4)GlcNAc] was enzymatically prepared by stepwise sugar-elongation on a water-soluble GlcNAc-bearing polyacrylamide. It was demonstrated that the flexible GlcNAc branches of the polymer chains allow quantitative galactosylation with bovine galactosyl transferase and partial sialylation by Trypanosoma cruzi trans-sialidase. Unsialylated N-acetyl-lactosamine side chains can be removed with beta-D-galactosidase and N-acetyl-beta-D-glucosaminidase. (C) 1994 Academic Press, Inc.
    ACADEMIC PRESS INC JNL-COMP SUBSCRIPTIONS, 英語, 研究論文(学術雑誌)
    ISSN:0006-291X, ORCID:41457119, Web of Science ID:WOS:A1994MY10100038
  • SYNTHETIC GLYCOCONJUGATES .3. AN EFFICIENT SYNTHESIS OF A GLYCOPROTEIN MODEL HAVING A LE(X)-TYPE TRISACCHARIDE SEQUENCE OF TUMOR-ASSOCIATED CARBOHYDRATE ANTIGEN
    SI NISHIMURA; K MATSUOKA; T FURUIKE; N NISHI; S TOKURA; K NAGAMI; S MURAYAMA; K KURITA
    MACROMOLECULES, 巻:27, 号:1, 開始ページ:157, 終了ページ:163, 1994年01月, [査読有り]
    A unique and efficient synthetic strategy for the macromolecule containing the tumor-associated antigenic oligosaccharide, Lewis x (Le(x)), is described. A novel standardized intermediate derived from an available 1,6-anhydro-beta-lactose remarkably facilitated the conventional synthetic route of a peracetate of Galp beta(1 --> 4) [Fucp alpha(1 --> 3)]GlcpNAc as an important precursor for the preparation of the targeted polymerizable glycoside. Introduction of an n-pentenyl group at the anomeric position into the peracetate of Le(x) through a reactive oxazoline derivative successfully afforded a new type of carbohydrate monomer. Copolymerization of the glycoside with acrylamide proceeded smoothly and gave a biochemically interesting glycoprotein model having a pendant Le(x) structure.
    AMER CHEMICAL SOC, 英語, 研究論文(学術雑誌)
    ISSN:0024-9297, ORCID:41457124, Web of Science ID:WOS:A1994MQ38500023
  • PREPARATION OF GLYCOPROTEIN MODELS - PENDANT-TYPE OLIGOSACCHARIDE POLYMERS
    S NISHIMURA; T FURUIKE; K MATSUOKA
    NEOGLYCOCONJUGATES, PT A, 巻:242, 開始ページ:235, 終了ページ:246, 1994年, [査読有り]
    ACADEMIC PRESS INC, 英語
    ISSN:0076-6879, ORCID:41457122, Web of Science ID:WOS:A1994BB94E00022
  • FLUORESCENT DERIVATIVES OF GLYCOPEPTIDES, OLIGOSACCHARIDES, AND GLYCOSIDES
    YC LEE; L BRAND; K RICE; KB LEE; RT LEE; K MATSUOKA; M QUENSENBERRY; PG WU
    JOURNAL OF CELLULAR BIOCHEMISTRY, 開始ページ:257, 終了ページ:257, 1994年, [査読有り]
    WILEY-LISS, 英語
    ISSN:0730-2312, ORCID:41457121, Web of Science ID:WOS:A1994NE25400835
  • SYNTHETIC GLYCOCONJUGATES .2. NORMAL-PENTENYL GLYCOSIDES AS CONVENIENT MEDIATORS FOR THE SYNTHESES OF NEW TYPES OF GLYCOPROTEIN MODELS
    SI NISHIMURA; K MATSUOKA; T FURUIKE; S ISHII; K KURITA; KM NISHIMURA
    MACROMOLECULES, 巻:24, 号:15, 開始ページ:4236, 終了ページ:4241, 1991年07月, [査読有り]
    The efficacy of n-pentenyl glycosides as excellent carbohydrate monomers in the syntheses of pseudoglycoproteins has been systematically demonstrated. A facile procedure for the preparation of novel glycoprotein models having pendant N,N'-diacetylchitobiose [beta-D-GlcpNAc-(1-->4)-beta-D-GlcpNAc] and N-acetyllactosamine [beta-D-Galp-(1-->4)-beta-D-GlcpNAc] was established on the basis of radical copolymerization of the n-pentenylated derivatives with acrylamide. These synthetic glycoconjugates exhibited good solubility in water and had high molecular weights. The sugar contents in the macromolecules could be regulated at will as the needs of the case demand. Specific adhesion of rat hepatocytes on these matrices was also examined to show that the matrix containing N-acetyllactosamine had especially high potentials.
    AMER CHEMICAL SOC, 英語, 研究論文(学術雑誌)
    ISSN:0024-9297, ORCID:41457126, Web of Science ID:WOS:A1991FY04700002
  • SYNTHETIC GLYCOCONJUGATES - SIMPLE AND POTENTIAL GLYCOPROTEIN MODELS CONTAINING PENDANT N-ACETYL-D-GLUCOSAMINE AND N,N'-DIACETYLCHITOBIOSE
    SI NISHIMURA; K MATSUOKA; K KURITA
    MACROMOLECULES, 巻:23, 号:18, 開始ページ:4182, 終了ページ:4184, 1990年09月, [査読有り]
    AMER CHEMICAL SOC, 英語
    ISSN:0024-9297, ORCID:41457127, Web of Science ID:WOS:A1990DX04200024
■ MISC
  • β-グルコシダーゼ酵素反応の1分子蛍光イメージング               
    飯塚怜; 利光郁美; 荒井啓克; 手塚俊博; 松岡浩司; 劉暁宇; 大久保幸太朗; 谷井孝至; 五十嵐圭日子; 鮫島正浩; 船津高志
    バイオイメージング, 巻:23, 号:2, 2014年
    ISSN:1342-2634, J-Global ID:201402279042678976
  • BIO R&D 糖鎖クラスター効果を利用したウイルス・毒素類の多目的検出薬の開発               
    幡野 健; 松岡 浩司
    バイオインダストリー, 巻:28, 号:3, 開始ページ:55, 終了ページ:59, 2011年03月
    シーエムシー出版, 日本語
    ISSN:0910-6545, CiNii Articles ID:40018715008, CiNii Books ID:AN10039203
  • 金ナノ微粒子表面に対する機能性糖鎖の新規導入法
    小山 哲夫; 幡野 健; 松岡 浩司
    埼玉大学地域オープンイノベーションセンター紀要, 巻:3, 開始ページ:49, 終了ページ:49, 2011年
    Multivalent structure with carbohydrate moieties and its biological properties have been studied. Novel method for synthesizing gold-nano-particles carrying carbohydrate moieties have been developed and the method is much more convenient than a traditional method. Expection of the glyco-gold-nanoparticle is display of multivalent carbohydrate moieties on the surface and show of effective interaction with pathogens. In addition it has capability of applying to diagnostric use such as medical test kit.
    埼玉大学総合研究機構地域オープンイノベーションセンター, 日本語
    CiNii Articles ID:120003088323
  • シロールをコアとした糖鎖担持カルボシランデンドリマーのレクチン検査薬としての評価<論文>
    佐伯 整; 幡野 健; 横田 洋大; 相澤 宏明; 小山 哲夫; 松岡 浩司; 照沼 大陽
    埼玉大学工学部紀要 第一部 論文集, 巻:42, 開始ページ:14, 終了ページ:18, 2008年
    A glycocluster periphery functionalized with lactose derivative possessing a silole moiety as a luminophore was synthesized. The photoluminescence spectrum of the glycocluster showed extremely strong emission at 475 nm and the absolute quantum yield was estimated to be 92% in water. The emission intensity was decreased by increasing the amount of peanut agglutinin (PNA), lactose-binding lectin, eventually to be nearly one-twentieth of the intensity in the case of absence of PNA. The fluorescence quenching of the glycocluster on mixing with PNA can be easily distinguished with the naked-eye observation under UV irradiation. Whereas no distinct change in the fluorescence properties of the glycoclyster was observed when wheat germ agglutinin (WGA) was employed.
    埼玉大学工学部, 日本語
    CiNii Articles ID:120005373728
  • タミフル耐性インフルエンザウィルス阻害剤の基礎研究(II)               
    松岡 浩司
    2008年
  • タミフル耐性インフルエンザウィルス阻害剤の基礎研究 (II)               
    松岡 浩司
    号:6(平成19年度), 2008年
  • 新規インフルエンザ特効薬2               
    松岡 浩司
    2008年
  • 新規インフルエンザ特効薬1               
    松岡 浩司
    2008年
  • 標的認識能を有する有機ケイ素-糖鎖ハイブリッド材料               
    照沼大陽; 松岡浩司; 幡野健
    未来材料, 巻:8, 号:6, 開始ページ:45, 終了ページ:50, 2008年
    エヌ・ティー・エス, 日本語
    ISSN:1346-0986, CiNii Articles ID:40016109130, CiNii Books ID:AA11501273
  • 糖鎖と有機ケイ素化合物の複合による新規機能材料               
    幡野健; 松岡浩司; 照沼大陽
    化学工業, 巻:59, 号:2, 開始ページ:95, 終了ページ:100, 2008年
    化学工業社, 日本語
    ISSN:0451-2014, CiNii Articles ID:40015811412, CiNii Books ID:AN00037245
  • アラビノガラクタン-プロテインの糖鎖のβ-グルクロニダーゼによる分解               
    古西智之; 小竹敬久; SORAYA Dina; 松岡浩司; 小山哲夫; 金子哲; 五十嵐圭日子; 鮫島正浩; 円谷陽一
    日本糖質学会年会要旨集, 巻:27th, 2007年
    J-Global ID:200902224219842160
  • タミフル耐性インフルエンザウィルス阻害剤の基礎研究               
    松岡 浩司
    2007年
  • 糖鎖の活性増幅とその応用               
    松岡浩司
    開始ページ:23, 終了ページ:26, 2007年
  • タミフル耐性インフルエンザウィルス阻害剤の基礎研究               
    松岡浩司
    巻:5(18年度), 開始ページ:529, 終了ページ:530, 2007年
  • 糖脂質Gb3を受容体とする細菌毒素、 Shiga toxin に対する阻害剤開発と治療への応用               
    渡邊 美帆; 松岡 浩司; 喜多 英二; 猪飼 桂; 矢ノ下 良平; 鮫島 勇次; 照沼 大陽; 名取 泰博; 西川 喜代孝
    脂質生化学研究, 巻:48, 開始ページ:130, 終了ページ:130, 2006年06月08日
    日本語
    ISSN:0285-1520, CiNii Articles ID:10024354830, CiNii Books ID:AN00102325
  • Design, Synthesis, and Biological Evaluation of Glyco-Materials               
    K. Matsuoka
    開始ページ:24, 終了ページ:25, 2006年
  • アレルギー関連糖鎖エピトープの合成と機能化に関する研究               
    松岡浩司
    号:4(17年度), 開始ページ:163, 終了ページ:165, 2006年
  • Thiosialoside Clusters as Inhibitors for Influenza Virus Neuraminidases               
    J.-I. Sakamoto; C. Takita; T. Koyama; K. Hatano; D. Terunuma; Y. Esumi; K. I.-P; J. Hidari; S. Yingsakmongkon; D. Miyamoto; W. Usawattanakul; T. Suzuki; Y. Suzuki; K. Matsuoka
    開始ページ:173, 2006年
  • Synthetic Construction of Novel Sugar―Amino Acid Hybrid Materials Using Typical Radical Polymerization Protocol               
    K. Matsuoka; Y. Goshu; T. Koyama; K. Hatano; D. Terunuma
    開始ページ:275, 2006年
  • Synthesis of a Series of Carbosilane Dendrimers Having Thioglycoside-type Sialic Acid Moieties               
    J.-I. Sakamoto; T. Koyama; Y. Esumi; H. Koshino; K. I.-P; J. Hidari; T. Suzuki; Y. Suzuki; K. Hatano; D. Terunuma; K. Matsuoka
    開始ページ:279, 2006年
  • Identification of the optimal structure required for a Shiga toxin neutralizer with oriented carbohydrates to function in the circulation               
    K Nishikawa; K Matsuoka; M Watanabe; K Igai; K Hino; K Hatano; A Yamada; N Abe; D Terunuma; H Kuzuhara; Y Natori
    巻:191, 号:12, 開始ページ:2097, 終了ページ:2105, 2005年06月
    Shiga toxin (Stx) is a major virulence factor of Stx-producing Escherichia coli. Recently, we developed a therapeutic Stx neutralizer with 6 trisaccharides of globotriaosyl ceramide, a receptor for Stx, in its dendrimer structure ( referred to as "SUPER TWIG [ 1] 6") to function in the circulation. Here, we determined the optimal structure of SUPER TWIG for it to function in the circulation and identified a SUPER TWIG with 18 trisaccharides, SUPER TWIG ( 2)18, as another potent Stx neutralizer. SUPER TWIGs ( 1)6 and ( 2)18 shared a structural similarity, a dumbbell shape in which 2 clusters of trisaccharides were connected via a linkage with a hydrophobic chain. The dumbbell shape was found to be required for formation of a complex with Stx that enables efficient uptake and degradation of Stx by macrophages and, consequently, for potent Stx-neutralizing activity in the circulation. We also determined the binding site of the SUPER TWIGs on Stx.
    英語
    DOI:https://doi.org/10.1086/430388
    DOI ID:10.1086/430388, ISSN:0022-1899, Web of Science ID:WOS:000229203900014
  • Synthesis of carbosilane dendrimers having peripheral mannose and mannobiose               
    T Mori; K Hatano; K Matsuoka; Y Esumi; EJ Toone; D Terunuma
    巻:61, 号:11, 開始ページ:2751, 終了ページ:2760, 2005年03月
    The mannose monosaccharide derivative, acetylthiopropyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (Man), and the mannobiose derivative, acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2,3',4',6'-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (alpha-1,3-Man), were synthesized respectively. These mannose derivatives were introduced into carbosilane dendrimer scaffolds of the zero and first generations. As a result, six carbosilane dendrimers were functionalized by Man and alpha-1,3-Man. Isothermal titration microcalorimetry was done to determine binding assay between mannose moieties of carbosilane dendrimer and concanavalin A. It was found that carbosilane dendrimers bound more efficiently to concanavalin A than free mannose (Me-alpha-Man) and mannobiose (Me-alpha-1,3-' Man). (c) 2005 Elsevier Ltd. All rights reserved.
    英語
    DOI:https://doi.org/10.1016/j.tet.2005.01.090
    DOI ID:10.1016/j.tet.2005.01.090, ISSN:0040-4020, CiNii Articles ID:80017259179, Web of Science ID:WOS:000227581000003
  • カルボシランデンドリマー・糖鎖複合材料の開発 : 大腸菌O157の産生するベロ毒素中和剤への応用<論文>
    幡野 健; 松岡 浩司; 照沼 大陽
    埼玉大学紀要, 工学部, 第1部論文集, 巻:1, 号:38, 開始ページ:40, 終了ページ:44, 2005年
    Carbosilane dendrimer periphery bearing globotiaose were synthesized by SN2 reaction of thiolate anion at aglycon of globotriaose and brominated carbosilane dendrimer. Binding assay of tree shapes of carbosilane dendrimers [Fan(0)3, Dumbbell(1)6 and Ball(1)12] were carried out. Vero toxin classified into two closely related subgroups, Stx1 and Stx2. Dumbbell(1)6 and Ball(1)12 markedly inhibited the cytotoxic activity of both Stx1 (0.22 and 0.16 μg/ml respectively) and Stx2 (2.3 and 1.3 μg/ml, respectively) toward Vero cells; whereas the IC50 of Fan(0)3 was more than 100 μg/ml. The result of the binding assay of these toxins suggested that Dumbbell(1)6 and Ball(1)12 bind to both Stx1 and Stx2 with high affinities. Furthermore, inhibitory effects of these dendrimers on the lethality of intravenously administered Stx2 in mice were investigated. Dumbbell(1)6 completely suppressed the lethal effect of Stx2 when administered along with the toxin. The dendrimer treated mice survived more than 2 months without any pathological symptoms.
    埼玉大学工学部, 日本語
    ISSN:1880-4446, CiNii Articles ID:120001370805
  • Syntheses and Biological Assay of a Series of Lacto-N-neotetraose Cluster using Carbosilane Dendrimer Scaffolds               
    Akihiro, Yamada; Ken Hatano; Koji Matsuoka; Yasuaki Esumi; Chie Aoki; Kazuya Hidari; Yasuo Suzuki; Daiyo Terunuma
    開始ページ:134, 2005年
  • Advantages of Carbosilane Dendrimer as a Carbohydrate Scaffold --Application to Artificial Receptor of E. Coli, Influenza and Dengue Virus--               
    Ken Hatano; Akihiro Yamada; Tetsuo Koyama; Koji Matsuoka; Daiyo Terunuma; Yasuaki Esumi; Kiyotaka Nishikawa; Yasuhiro Natori; Kazuya Hidari; Yasuo Suzuki
    開始ページ:78, 2005年
  • Synthesis and property of carbosilane dendrimers functionalizing peripheral mannose moieties               
    T Mori; K Hatano; K Matsuoka; Y Esumi; EJ Toone; D Terunuma
    巻:14, 号:11, 開始ページ:1093, 終了ページ:1093, 2004年11月
    英語, 研究発表ペーパー・要旨(国際会議)
    ISSN:0959-6658, Web of Science ID:WOS:000224206400146
  • Synthesis and biological evaluation of glycopolymer as Shiga toxin neutralizer               
    K Matsuoka; A Miyagawa; K Nishikawa; M Watanabe; Y Natori; E Kita; T Koyama; K Hatano; D Terunuma
    巻:14, 号:11, 開始ページ:1194, 終了ページ:1194, 2004年11月
    英語, 研究発表ペーパー・要旨(国際会議)
    ISSN:0959-6658, Web of Science ID:WOS:000224206400508
  • シクロデキストリンの化学修飾(ミニレビュー)               
    松岡浩司
    日本農芸化学会誌, 巻:78, 号:9, 開始ページ:863, 終了ページ:865, 2004年
    Japan Society for Bioscience, Biotechnology, and Agrochemistry, 日本語
    DOI:https://doi.org/10.1271/nogeikagaku1924.78.863
    DOI ID:10.1271/nogeikagaku1924.78.863, ISSN:0002-1407, CiNii Articles ID:10013521657, CiNii Books ID:AN00196191
  • 化学合成と酵素合成によるN-アセチルラクトサミンクラスターの構築               
    松岡浩司; 照沼大陽
    埼玉大学地域共同研究センター紀要, 巻:4, 開始ページ:86, 2004年
  • N-アセチルラクトサミン誘導体の合成とクラスター化に関する研究
    松岡 浩司; 照沼 大陽
    埼玉大学地域共同研究センター紀要, 巻:3, 開始ページ:61, 終了ページ:61, 2002年
    埼玉大学地域共同研究センター, 日本語
    ISSN:1347-4758, CiNii Articles ID:120001371534
  • N型糖鎖を認識するユビキチンリガーゼ               
    吉田 雪子; 川崎 博史; 岩井 一宏; 千葉 智樹; 鈴木 俊顕; 松岡 浩司; 田中 啓二; 田井 直
    生化学, 巻:73, 号:8, 開始ページ:696, 終了ページ:696, 2001年08月
    (公社)日本生化学会, 日本語
    ISSN:0037-1017, 医中誌Web ID:2002073012
  • 新規N-アセチルラクトサミン誘導体の合成と応用に関する研究
    松岡 浩司; 照沼 大陽
    埼玉大学地域共同研究センター紀要, 巻:2, 開始ページ:132, 終了ページ:132, 2001年
    埼玉大学地域共同研究センター, 日本語
    ISSN:1347-4758, CiNii Articles ID:120001389851
  • 側鎖に光学活性な置換基を有する水溶性ポリシランの合成と評価               
    照沼 大陽; 南雲 公二; 鎌田 憲彦; 松岡 浩司; 葛原 弘美
    電子情報通信学会技術研究報告. OME, 有機エレクトロニクス, 巻:99, 号:319, 開始ページ:5, 終了ページ:10, 1999年09月21日
    一般社団法人電子情報通信学会, 日本語
    ISSN:0913-5685, CiNii Articles ID:110003301105, CiNii Books ID:AN10013334
  • 2糖トレハロースを出発物としたL-イズロン酸の新規合成法               
    比能洋; 黒沢英弘; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会講演予稿集, 巻:76th, 号:2, 1999年
    ISSN:0285-7626, J-Global ID:200902157463555646
  • 光学活性基を側鎖に有するポリシランの合成とその構造               
    照沼 大陽; 南雲 公二; 天野 裕貴; 鎌田 憲彦; 松岡 浩司; 葛原 弘美
    電子情報通信学会技術研究報告. OME, 有機エレクトロニクス, 巻:98, 号:38, 開始ページ:7, 終了ページ:12, 1998年05月06日
    ヘキシルフェニルポリシランをWurtz法により合成し、Friedel-Crafts反応によりクロロメチル基を導入した。モデル化合物を用いたクロロメチル化の結果からクロロメチル基がパラ位に導入されていることが分かった。さらに、クロロメチル化したポリマーに光学活性なN, N-Dimethyl-α-methyl-benzylamineを作用させて側鎖に光学活性基を有するポリシランを得た。エタノール中でCDスペクトルの吸収が観測されたことからこのポリシランは片方のラセン構造をとっていることが分かった。
    一般社団法人電子情報通信学会, 日本語
    CiNii Articles ID:110003300910, CiNii Books ID:AN10013334
  • トレハロースのL-イドース含有2糖への変換反応               
    比能洋; 黒沢英弘; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会講演予稿集, 巻:74th, 号:2, 1998年
    ISSN:0285-7626, J-Global ID:200902172522778718
  • 両親媒性キトオリゴ糖誘導体の合成 I 長鎖アシルアミノ基を活用したグリコシル化反応               
    海野篤; 比能洋; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会講演予稿集, 巻:72nd, 号:2, 1997年
    ISSN:0285-7626, J-Global ID:200902159244630155
  • 両親媒性キトオリゴ糖誘導体の合成 II 2本の疎水性長鎖を結合した3糖,5糖,7糖の合成               
    比能洋; 海野篤; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会講演予稿集, 巻:72nd, 号:2, 1997年
    ISSN:0285-7626, J-Global ID:200902167889880159
  • 分子集合能を持つキトビオース誘導体の合成               
    比能洋; 海野篤; 松岡浩司; 照沼大陽; 葛原弘美
    キチン・キトサン研究, 巻:3, 号:2, 1997年
    ISSN:1340-9778, J-Global ID:200902135023783848
  • キトオリゴ糖ミセルの合成研究               
    比能洋; 海野篤; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会講演予稿集, 巻:70th, 号:2, 1996年
    ISSN:0285-7626, J-Global ID:200902125906647361
  • A Simple Method for the Preparation of Pseudo-Glycoproteins Containing Pendant N-Acetyl-D-glucosamine and N,N’-Diacetylchitobiose               
    Nishimura; S.-I.; Matsuoka; Kurita, K.; ”
    開始ページ:238, 終了ページ:239, 1990年10月, [査読有り]
    英語, 研究発表ペーパー・要旨(国際会議)
■ 書籍等出版物
  • K. Matsuoka, N. Taniguchi, A. Suzuki, Y. Ito, H. Narimatsu, T. Kawasaki, and S. Hase, (Eds.) Sugar Polymers (Dendrimers and Pendant-type Linear Polymers) Experimental Glycoscience               
    Springer, 2008年
  • K. Matsuoka, N. Taniguchi, A. Suzuki, Y. Ito, H. Narimatsu, T. Kawasaki, and S. Hase, (Eds.) Sugar Polymers (Dendrimers and Pendant-type Linear Polymers) Experimental Glycoscience               
    Springer, 2008年
  • K. Matsuoka, K. Hatano, and D. Terunuma, H. Yuasa (Ed) Glycodendrimers using carbosilanes as core scaffolds (Review) Nanotechnology in Carbohydrate Chemistry               
    Transworld Research Network, 2006年
  • K. Matsuoka, K. Hatano, and D. Terunuma, H. Yuasa (Ed) Glycodendrimers using carbosilanes as core scaffolds (Review) Nanotechnology in Carbohydrate Chemistry               
    Transworld Research Network, 2006年
  • 松岡浩司 糖鎖高分子 (デンドリマー, グライコマテリアル) 未来を拓く糖鎖科学               
    金芳堂, 2005年
  • 松岡浩司, 幡野健, 照沼大陽 機能性デンドリマーの合成 糖鎖化学の最先端技術               
    シーエムシー出版, 2005年
  • 松岡浩司, 幡野健, 森知紀, 照沼大陽 グライコデンドリマー 糖鎖科学の新展開               
    エヌ・ティー・エス出版, 2005年
  • 松岡浩司 糖鎖高分子 (デンドリマー, グライコマテリアル) 未来を拓く糖鎖科学               
    金芳堂, 2005年
  • 松岡浩司, 幡野健, 照沼大陽 機能性デンドリマーの合成 糖鎖化学の最先端技術               
    シーエムシー出版, 2005年
  • 松岡浩司, 幡野健, 森知紀, 照沼大陽 グライコデンドリマー 糖鎖科学の新展開               
    エヌ・ティー・エス出版, 2005年
  • 照沼大陽, 松岡浩司, 幡野健 カルボシランデンドリマー-糖鎖複合物質--大腸菌O157の産生するベロ毒素中和剤の開発-- 21世紀の有機ケイ素化学               
    シーエムシー出版, 2004年
  • 照沼大陽, 松岡浩司, 幡野健 カルボシランデンドリマー-糖鎖複合物質--大腸菌O157の産生するベロ毒素中和剤の開発-- 21世紀の有機ケイ素化学               
    シーエムシー出版, 2004年
  • K. Matsuoka, S.-I. Nishimura, and Y. C. Lee Preparation of Fluorescence-Labeled Neoglycolipids for Ceramide Glycanase Assays Methods in Enzymol.               
    Academic Preess, 1997年
  • K. Matsuoka, S.-I. Nishimura, and Y. C. Lee Preparation of Fluorescence-Labeled Neoglycolipids for Ceramide Glycanase Assays Methods in Enzymol.               
    Academic Preess, 1997年
  • Glycoprotein Models from N,N’-Diacetylchitobiose and the Related Oligosaccharides               
    Nishimura, S.-I.; Matsuoka, K.; Furuike, T.; Kurita, K.
    International Symposium on Chitin Derivatives in Life Science, 1992年05月, [査読有り]
    英語, 学術書
■ 講演・口頭発表等
  • N-結合型糖ペプチドの基礎的な合成研究               
    松山恭子; 鈴木美穂; 小山哲夫; 幡野健; 照沼大陽; 松岡浩司
    日本化学会第85回春季年会(横浜)講演予稿集, 3F2-02, 2005年03月
    日本語, 口頭発表(一般)
  • 糖鎖デンドリマーの合成と酵素による糖鎖伸長反応の検討               
    金子礼奈; 小山哲夫; 江角保明; 幡野健; 照沼大陽; 松岡浩司
    日本化学会第85回春季年会(横浜)講演予稿集, 3F2-14, 2005年03月
    日本語, 口頭発表(一般)
  • 新規ノイラミニダーゼ阻害剤の合成研究 (I)               
    坂本純一; 小山哲夫; 江角保明; 幡野健; 照沼大陽; 松岡浩司
    日本化学会第85回春季年会(横浜)講演予稿集, 3F2-15, 2005年03月
    日本語, 口頭発表(一般)
  • インフルエンザウイルス阻害能を指向したシアリルラクトサミン担持カルボシランデンドリマーの合成               
    森知紀; 幡野健; 松岡浩司; 江角保明; 左一八; 鈴木康夫; 照沼大陽
    日本化学会第85回春季年会(横浜)講演予稿集, 3F2-16, 2005年03月
    日本語, 口頭発表(一般)
  • チオグリコシド型グロボ3糖誘導体の合成研究 (2)               
    黒澤直; 小山哲夫; 江角保明; 幡野健; 照沼大陽; 松岡浩司
    日本化学会第85回春季年会(横浜)講演予稿集, 2A2-10, 2005年03月
    日本語, 口頭発表(一般)
  • 糖鎖含有カルボシランデンドリマーの合成研究 (VII)-デンドリマー中心元素の変化によるベロ毒素阻害活性への効果-               
    山田明宏; 幡野健; 松岡浩司; 江角保明; 西川喜代孝; 名取泰博; 照沼大陽
    日本化学会第85回春季年会(横浜)講演予稿集, 2C5-16, 2005年03月
    日本語, 口頭発表(一般)
  • 側鎖に液晶分子を有する新規ポリシランの合成(1)               
    高橋英記; 幡野健; 青木良夫; 松岡浩司; 鎌田憲彦; 照沼大陽
    日本化学会第85回春季年会(横浜)講演予稿集, 1PA24, 2005年03月
    日本語, ポスター発表
  • 1,4-ジシラビシクロ[2,2,2]オクタンの合成とその反応性に関する研究               
    相澤宏明; 幡野健; 松岡浩司; 照沼大陽
    日本化学会第85回春季年会(横浜)講演予稿集, 1C5-21, 2005年03月
    日本語, 口頭発表(一般)
  • 糖鎖クラスターの構築: 工学的アプローチ,               
    松岡浩司
    東京糖鎖研究会GlycoTOKYO2004 Symposium (SaitamaUniv.), p. 1, 2005年03月, [招待有り]
    日本語, 口頭発表(招待・特別)
  • 糖鎖担持カルボシランデンドリマー製剤の設計技術開発に関する研究               
    照沼大陽; 松岡浩司
    平成16年度厚生労働省科学研究費研究成果等普及啓発事業 萌芽的先端医療技術推進研究, ナノメディシン研究成果発表会, pp. 5-6, 2005年02月
    日本語, 口頭発表(一般)
  • Synthesis;Biological Evaluation of;Glycopolymer as;Shiga Toxin;Neutralizer               
    K. Matsuoka; A. Miyagawa; K. Nishikawa; M. Watanabe; Y. Natori; E. Kita; T. Koyama; K. Hatano; D. Terunuma
    US/JAPAN GLYCO2004, Joint Meeting of the Society for Glycobiology and the Japanese Society of Carbohydrate Research (Hawaii, USA), November 17 – 20, 2004, #500, p. 1194, 2004年11月
    2004年11月 - 2004年11月, 日本語, ポスター発表
  • Synthesis and Property of Carbosilane Dendrimers Functionalizing Peripheral Mannose Moieties               
    T. Mori; K. Hatano; K. Matsuoka; Y. Esumi; E. J. Toone; D. Terunuma
    US/JAPAN GLYCO2004, Joint Meeting of the Society for Glycobiology and the Japanese Society of Carbohydrate Research (Hawaii, USA), November 17 – 20, 2004, #138, p. 1093, 2004年11月
    英語, ポスター発表
  • N-結合型糖ペプチドの基礎的な合成研究               
    松山恭子; 小山哲夫; 幡野健; 照沼大陽; 松岡浩司
    有機合成化学協会第86回有機合成シンポジウム(早稲田)講演要旨集, P-7, pp. 128-129, 2004年11月
    日本語, ポスター発表
  • グロボ三糖含有カルボシランデンドリマーライブラリの構築               
    小山哲夫; 山田明宏; 幡野健; 松岡浩司; 照沼大陽; 名取泰博; 西川喜代孝
    有機合成化学協会第86回有機合成シンポジウム(早稲田)講演要旨集, P-4, pp. 122-123, 2004年11月
    日本語, ポスター発表
  • 糖鎖含有カルボシランデンドリマーの合成研究(VII)               
    山田明宏; 幡野健; 松岡浩司; 照沼大陽; 江角保明; 左一八; 鈴木康夫; 西川喜代孝; 名取泰博
    第9回ケイ素化学協会シンポジウム(渋谷)講演要旨集, P95, p. 125, 2004年10月
    日本語, ポスター発表
  • シアリルラクトサミン担持カルボシランデンドリマーの合成,               
    森知紀; 幡野健; 松岡浩司; 江角保明; 左一八; 鈴木康夫; 照沼大陽
    第9回ケイ素化学協会シンポジウム(渋谷)講演要旨集, P49, p. 79, 2004年10月
    日本語, ポスター発表
  • 多価型ベロ毒素中和剤の開発               
    松岡浩司; 宮川淳; 幡野健; 照沼大陽; 西川喜代孝; 渡邉美帆; 名取泰博; 喜多英二
    高分子学会第53回高分子討論会(札幌)講演予稿集, 3W11, 53 (2), pp. 5416-5417, 2004年09月, [招待有り]
    日本語, 口頭発表(招待・特別)
  • シアリルラクトサミン担持カルボシランデンドリマーの合成研究               
    森知紀; 幡野健; 松岡浩司; 江角保明; 左一八; 鈴木康夫; 照沼大陽
    高分子学会第53回高分子討論会(札幌)講演予稿集, 2Pe175, 53 (2), p. 5278, 2004年09月
    日本語, ポスター発表
  • 糖鎖含有カルボシランデンドリマーの合成研究;パラグロボシド含有カルボシランデンドリマーの合成と評価               
    山田明宏; 幡野健; 松岡浩司; 照沼大陽; 青木千恵; 左一八; 鈴木康夫; 江角保明
    高分子学会第53回年次大会(神戸)講演予稿集, IIPe165, 53 (1), p. 2088, 2004年05月
    日本語, ポスター発表
  • 糖鎖含有カルボシランデンドリマーの合成研究 (VI)-デングウイルス阻害剤の合成と生物学的評価-               
    山田明宏; 幡野 健; 松岡浩司; 照沼大陽; 青木千恵; 左一八; 鈴木康夫; 江角保明
    高分子学会第53回年次大会(神戸)講演予稿集, IH13, 53 (1), p. 1888, 2004年05月
    日本語, 口頭発表(一般)
  • マンノースおよびその二糖によって機能化したカルボシランデンドリマーの合成と性質               
    森知紀; 幡野健; 松岡浩司; 江角保明; 照沼大陽; Eric J.Toone
    高分子学会第53回年次大会(神戸)講演予稿集, IH12, 53 (1), p. 1887, 2004年05月
    日本語, 口頭発表(一般)
  • N-アセチルラクトサミン担持カルボシランデンドリマーの合成               
    幡野健; 森知紀; 大田和拓己; 松岡浩司; 江角保明; 照沼大陽; 左一八; 鈴木康夫
    高分子学会第53回年次大会(神戸)講演予稿集, IH10, 53 (1), p. 1885, 2004年05月
    日本語, 口頭発表(一般)
  • シクロデキストリンの化学修飾               
    松岡浩司
    日本農芸化学会2004年度大会(広島)講演要旨集, SY-11-6, p. 435, 2004年03月, [招待有り]
    日本語, 口頭発表(招待・特別)
  • 新規シアル酸供与体の合成と反応性の検討               
    翁長朝典; 小山哲夫; 坂入信夫; 幡野健; 松岡浩司; 照沼大陽
    日本化学会第84回春季年会(西宮)講演予稿集, 4J2-45, p.1039, 2004年03月
    日本語, 口頭発表(一般)
  • シアリルラクトース含有カルボシランデンドリマー群の合成研究               
    翁長朝典; 小山哲夫; 江角保明; 鈴木康夫; 幡野健; 松岡浩司; 照沼大陽
    日本化学会第84回春季年会(西宮)講演予稿集, 4J2-44, p.1039, 2004年03月
    日本語, 口頭発表(一般)
  • チオグリコシド結合型グロボ3糖誘導体の合成研究               
    黒澤直; 小山哲夫; 幡野健; 松岡浩司; 照沼大陽; 江角保明
    日本化学会第84回春季年会(西宮)講演予稿集, 4J2-32, p.1036, 2004年03月
    日本語, 口頭発表(一般)
  • ナノサイズで制御された糖鎖クラスター型ベロ毒素中和剤の開発               
    松岡浩司; 幡野健; 西川喜代孝; 名取泰博; 喜多英二; 照沼大陽
    第2回ナノテクノロジー総合シンポジウム(有明)講演予稿集, pp. 258-259, 2004年03月
    日本語, 口頭発表(一般)
  • 糖鎖担持カルボシランデンドリマーの合成研究(IV)−ベロ毒素中和剤としての最適構造の探索−               
    山田明宏; 阿部展久; 森知紀; 小山哲夫; 幡野健; 松岡浩司; 照沼大陽; 日野久美子; 西川喜代孝; 名取泰博; 江角保明
    ケイ素化学協会第8回ケイ素化学協会シンポジウム(京都)講演要旨集, P80, p. 108, 2003年10月
    日本語, ポスター発表
  • マンノース担持カルボシランデンドリマーの合成               
    森知紀; 幡野健; 松岡浩司; 照沼大陽
    ケイ素化学協会第8回ケイ素化学協会シンポジウム(京都)講演要旨集, P40, p. 68, 2003年10月
    日本語, ポスター発表
  • アセチレン―オリゴシラン複合型高分子の合成と物性評価に関する研究               
    江面佳代子; 幡野健; 松岡浩司; 照沼大陽
    ケイ素化学協会第8回ケイ素化学協会シンポジウム(京都)講演要旨集, P4, p. 32, 2003年10月
    日本語, ポスター発表
  • ケイ素橋頭位化合物の合成に関する基礎研究               
    相澤宏明; 幡野健; 松岡浩司; 照沼大陽
    ケイ素化学協会第8回ケイ素化学協会シンポジウム(京都)講演要旨集, P1, p. 29, 2003年10月
    日本語, ポスター発表
  • マンノースおよびそのオリゴ糖を担持したカルボシランデンドリマーの合成               
    森知紀; 幡野健; 松岡浩司; 照沼大陽
    高分子学会第52回高分子討論会(山口)講演予稿集IIPe013, p. 1386, 2003年09月
    日本語, ポスター発表
  • 酵素を模倣したメチル化-シクロデキストリン類の合成研究               
    吉田順子; 松岡浩司; 小山哲夫; 幡野健; 照沼大陽
    シクロデキストリン学会第21回シクロデキストリンシンポジウム(札幌)講演要旨集、B10, pp. 197-198, 2003年09月
    日本語, 口頭発表(一般)
  • 特定炭素を化学修飾したメチル化-シクロデキストリンの合成と評価               
    吉田順子; 松岡浩司; 小山哲夫; 幡野健; 照沼大陽
    日本糖質学会第24回日本糖質学会年会(横浜)講演要旨集, P2-04, p. 108, 2003年07月
    日本語, ポスター発表
  • インフルエンザウィルス阻害能を有する糖鎖クラスターの合成研究               
    大田和拓巳; 松岡浩司; 小山哲夫; 西村紳一郎; 江角保明; 幡野健; 照沼大陽
    日本糖質学会第24回日本糖質学会年会(横浜)講演要旨集, P2-02, p. 107, 2003年07月
    日本語, ポスター発表
  • N-アセチルラクトサミンを基盤とした糖鎖クラスターの合成研究               
    松岡浩司; 大田和拓巳; 幡野健; 照沼大陽
    第5回グリコクラスター公開シンポジウム(札幌)講演要旨集, I, p. 12, 2003年07月, [招待有り]
    日本語, 口頭発表(一般)
  • Development of Dialyzer as Verotoxin Eliminator using Glycoconjugate Polymer               
    Miyagawa, A.; Kasuya, M.C.Z.; Matsuoka, K.; Hatanaka, K.
    12th European Carbohydrate Symposium (Grenoble, France), July 6 – 11, 2003, PD 004, 2003年07月
    2003年07月 - 2003年07月, 英語, ポスター発表
  • Novel N-Acetyllactosamine Clusters using Carbosilane Scaffolds               
    Ohtawa T.; Matsuoka K.; Koyama T.; Esumi Y.; Hatano K.; Terunuma D.; Nishimura S. -I.
    12th European Carbohydrate Symposium (Grenoble, France), July 6 – 1112th European Carbohydrate Symposium (Grenoble, France), July 6 – 11, 2003, PB120, 2003年07月
    2003年07月 - 2003年07月, 英語, ポスター発表
  • 直鎖ポリマーを基材とした高親和性ベロ毒素阻害剤の開発               
    渡邊美帆; 松岡浩司; 喜多英二; 猪飼桂; 東伸岳; 宮川淳; 渡邊敏之; 矢ノ下良平; 鮫島勇次; 照沼大陽; 西川喜代孝; 名取泰博
    第7回 腸管出血性大腸菌感染症シンポジウム, 2003年06月
    日本語, 口頭発表(一般)
  • Carbohydrate-containing linear polymers that neutralize Shiga toxins               
    Watanabe, M.; Nishikawa, K.; Matsuoka, K.; Higashi, N.; Igai, K.; Miyagawa, A.; Watanabe, T.; Yanoshita, R.; Samejima, Y.; Terunuma, D.; Kita, E.; Natori, Y.
    5th Int. Symp. on ‘Shiga Toxin (Verocytotoxin)-producing Escherichia coli Infections (VTEC2003) (Edinburgh EICC, Scotland), June 6 – 11, 2003, P167, 2003年06月
    2003年06月 - 2003年06月, 英語, ポスター発表
  • ベロ毒素中和剤の合成研究(III) 中和能と構造活性相関               
    竹澤豊; 松岡浩司; 小山哲夫; 阿部展久; 山田明宏; 森知紀; 名取泰博; 西川喜代孝; 江角保明; 幡野健; 照沼大陽
    有機合成化学協会第83回有機合成シンポジウム(江東)講演要旨集, I-6, pp. 33-36, 2003年06月
    日本語, 口頭発表(一般)
  • 糖鎖含有カルボシランデンドリマーの合成研究(II)               
    山田明宏; 阿部展久; 森知紀; 幡野健; 松岡浩司; 照沼大陽; 西川喜代孝; 名取泰博; 江角保明
    高分子学会第52回年次大会(名古屋)講演予稿集 IIPf138, p. 1063, 2003年05月
    日本語, ポスター発表
  • 糖鎖含有カルボシランデンドリマーの合成研究(I) ベロ毒素中和剤としてのアグリコン部分の鎖長の影響               
    小山哲夫; 竹澤 豊; 名取泰博; 西川喜代孝; 江角保明; 森知紀; 幡野健; 松岡浩司; 照沼大陽
    高分子学会第52回年次大会(名古屋)講演予稿集 IIPe137, p. 1063, 2003年05月
    日本語, ポスター発表
  • ベロ毒素中和剤の合成研究(II) Gb3含有新規カルボシランデンドリマー群の活性相関               
    小山哲夫; 竹澤 豊; 名取泰博; 西川喜代孝; 江角保明; 幡野 健; 松岡浩司; 照沼大陽
    日本化学会第83回春季年会(早稲田)講演予稿集 2G2-50, p. 953, 2003年03月
    日本語, 口頭発表(一般)
  • ベロ毒素中和剤の合成研究(I) Gb3含有新規カルボシランデンドリマー群の合成               
    竹澤 豊; 小山哲夫; 名取泰博; 西川喜代孝; 江角保明; 幡野 健; 松岡浩司; 照沼大陽
    日本化学会第83回春季年会(早稲田)講演予稿集 2G2-49, p. 953, 2003年03月
    日本語, 口頭発表(一般)
  • 両親媒性ポリシランの合成とそのLB膜化               
    森泉幸也; 幡野健; 松岡浩司; 鎌田憲彦; 照沼大陽
    日本化学会第83回春季年会(早稲田)講演予稿集 1H3-26, p. 385, 2003年03月
    日本語, 口頭発表(一般)
  • 両親媒性オリゴシランの合成とそのLB膜への応用               
    斎藤和久; 幡野健; 松岡浩司; 鎌田憲彦; 江角保明; 照沼大陽
    日本化学会第83回春季年会(早稲田)講演予稿集 1H3-25, p. 385, 2003年03月
    日本語, 口頭発表(一般)
  • ベロ毒素中和剤としてのカルボシランデンドリマーにおける担持糖鎖数の効果               
    山田明宏; 阿部展久; 森知紀; 幡野健; 松岡浩司; 照沼大陽; 西川喜代孝; 名取泰博; 江角保明
    日本化学会第83回春季年会(早稲田)講演予稿集 1C6-53, p. 832, 2003年03月
    日本語, 口頭発表(一般)
  • オリゴシランの末端官能基化とその応用に関する研究               
    斎藤和久; 幡野健; 松岡浩司; 鎌田憲彦; 江角保明; 照沼大陽
    ケイ素化学協会第7回ケイ素化学協会シンポジウム(神奈川)講演要旨集 P49, p. 75, 2002年11月
    日本語, ポスター発表
  • 病原性大腸菌O157中和剤としての糖鎖担持カルボシランデンドリマーの合成と評価               
    山田明宏; 幡野健; 松岡浩司; 照沼大陽; 西川喜代孝; 名取泰博; 江角保明
    ケイ素化学協会第7回ケイ素化学協会シンポジウム(神奈川)講演要旨集 P48, p. 74, 2002年11月
    日本語, ポスター発表
  • 9,10-ジシラトリプチセンの新規合成法の開発と応用               
    幡野健; 栗原琢; 松岡浩司; 照沼大陽
    ケイ素化学協会第7回ケイ素化学協会シンポジウム(神奈川)講演要旨集 P47, p. 73, 2002年11月
    日本語, ポスター発表
  • 病原性大腸菌O-157中和剤としての糖鎖ミカルボシランデンドリマー複合材料における骨格効果               
    山田明宏; 幡野健; 松岡浩司; 照沼大陽; 西川喜代孝; 名取泰博; 江角保明
    高分子学会第51回高分子討論会(北九州)講演予稿集 II Pa023, p. 1486, 2002年10月
    日本語, ポスター発表
  • 病原性大腸菌O-157中和剤としての糖鎖担持カルボシランデンドリマーの合成と評価               
    山田明宏; 幡野健; 松岡浩司; 照沼大陽; 西川喜代孝; 名取泰博; 江角保明
    高分子学会第51回高分子討論会(北九州)講演予稿集 II C13, p. 1277-1278, 2002年10月
    日本語, 口頭発表(一般)
  • 糖鎖高分子を用いた病原性タンパク質除去装置の開発               
    宮川淳; 粕谷マリアカルメリタ; 畑中研一; 松岡浩司
    高分子学会第51回高分子討論会(北九州)講演予稿集I U15, p. 3376-3377, 2002年10月
    日本語, 口頭発表(一般)
  • 特定炭素を化学修飾したβ-シクロデキストリン類の合成研究               
    吉田順子; 松岡浩司; 小山哲夫; 幡野健; 照沼大陽
    日本糖質学会第23回日本糖質学会年会(横浜)講演要旨集 PII-08, p. 112, 2002年08月
    日本語, ポスター発表
  • 新規N-アセチルラクトサミン誘導体の合成と応用               
    大田和拓巳; 松岡浩司; 小山哲夫; 西村紳一郎; 江角保明; 幡野健; 照沼大陽
    日本糖質学会第23回日本糖質学会年会(横浜)講演要旨集 PII-07, p. 112, 2002年08月
    日本語, ポスター発表
  • シアリルラクトース含有カルボシランデンドリマー群の合成研究               
    翁長朝典; 松岡浩司; 小山哲夫; 江角保明; 幡野健; 照沼大陽
    日本糖質学会第23回日本糖質学会年会(横浜)講演要旨集 PII-03, p. 110, 2002年08月
    日本語, ポスター発表
  • グロボ3 糖を担持する新規糖鎖クラスターの合成               
    竹澤豊; 松岡浩司; 小山哲夫; 幡野健; 照沼大陽; 江角保明
    日本糖質学会第23回日本糖質学会年会(横浜)講演要旨集 PII-02, p. 109, 2002年08月
    日本語, ポスター発表
  • 機能材料としての糖鎖クラスター               
    松岡浩司
    日本糖質学会第23回日本糖質学会年会(横浜)講演要旨集 SC-04, p. 23【企画講演】, 2002年08月, [招待有り]
    日本語, 口頭発表(招待・特別)
  • 末端にグロボ3 糖を導入した新規カルボシランデンドリマーの合成               
    小山哲夫; 陳 珊珊; 幡野 健; 松岡浩司; 江角保明; 照沼大陽
    日本糖質学会第23回日本糖質学会年会(横浜)講演要旨集 PI-11, p. 78, 2002年08月
    日本語, ポスター発表
  • カルボシランをコアとしたN-アセチルラクトサミンクラスターの合成研究               
    松岡浩司; 大田和拓巳; 赤木隆史; 小山哲夫; 西村紳一郎; 江角保明; 幡野健; 照沼大陽
    日本糖質学会第23回日本糖質学会年会(横浜)講演要旨集 PI-06, p. 75, 2002年08月
    日本語, ポスター発表
  • Novel N-Acetyllactosamine Derivative and Its Potential Reactivity as A Glycosyl Donor               
    Matsuoka, K.; Ohtawa, T.; Hinou, H.; Koyama, T.; Esumi, Y.; Nishimura, S.-I.; Hatano, K.; Terunuma, D.
    XXIst International Carbohydrate Symposium (Cairns, Australia), July 7 – 12, 2002, PP155, 2002年07月
    2002年07月 - 2002年07月, 英語, ポスター発表
  • Host Range of Influenza Viruses and Approach to Develop New Anti-Influenza Drugs               
    Suzuki, Y.; Suzuki, T.; Miyamoto, D.; Hidari; K. I.-P.J.; Guo, C.-T.; Ito, T.; Kanie, O.; Kida, H.; Nishimura, S.-I.; Matsuoka, K.; Terunuma, D.; Kawaoka, Y.
    XXIst International Carbohydrate Symposium (Cairns, Australia), July 7 – 12, 2002, OP058, 2002年07月
    2002年07月 - 2002年07月, 英語, 口頭発表(一般)
  • N-Glycans Are Recognized by E3 Ubiquitin-Ligase               
    Yoshida, Y.; Matsuoka, K.; Chiba, T.; Suzuki, T.; Tanaka, K.; Tai, T.
    XXIst International Carbohydrate Symposium (Cairns, Australia), July 7 – 12, 2002, OP044, 2002年07月
    2002年07月 - 2002年07月, 英語, 口頭発表(一般)
  • Synthesis of Polyacrylamide Carrying Globotriose Derivative for Immobilization on Cellulose Materials               
    Miyagawa, A.; Kasuya; M. C. Z.; Hatanaka, K.; Matsuoka, K.
    XXIst International Carbohydrate Symposium (Cairns, Australia), July 7 – 12, 2002, Abstract PP160, 2002年07月
    2002年07月 - 2002年07月, 英語, ポスター発表
  • ガラビオース担持カルボシランデンドリマーの合成               
    山田明宏; 幡野健; 松岡浩司; 照沼大陽
    高分子学会第51回年次大会(横浜)講演予稿集 IIPc019, p. 331, 2002年05月
    日本語, ポスター発表
  • グロボ3糖担持カルボシランデンドリマーの合成—脂溶性基の効果の検討               
    陳 珊珊; 竹澤 豊; 松岡浩司; 幡野健; 照沼大陽
    高分子学会第51回年次大会(横浜)講演予稿集 IIPd018, p. 330, 2002年05月
    日本語, ポスター発表
  • カルボシラン-ポリイミン複合型デンドリマーの合成と応用               
    阿部展久; 幡野健; 松岡浩司; 照沼大陽
    高分子学会第51回年次大会(横浜)講演予稿集 IIPa015, p. 315, 2002年05月
    日本語, ポスター発表
  • N-アセチルラクトサミン誘導体の改良合成法とそのクラスター化               
    松岡浩司; 照沼大陽
    第4回グリコクラスターシンポジウム(札幌)講演要旨集 03, p. 21, 2002年05月
    日本語, 口頭発表(一般)
  • N-アセチルラクトサミン誘導体の効率的合成法とカルボシランデンドリマーへの導入法の検討               
    大田和拓己; 松岡浩司; 西村紳一郎; 江角保明; 幡野 健; 照沼大陽
    日本化学会第81回春季年会(早稲田)講演予稿集 1F6-30, p. 948, 2002年03月
    日本語, 口頭発表(一般)
  • ベロ毒素中和活性の及ぼすカルボシランデンドリマーサイズの効果               
    阿部展久; 山田明宏; 森知紀; 名取泰博; 西川喜代孝; 江角保明; 幡野 健; 松岡浩司; 照沼大陽
    日本化学会第83回春季年会(早稲田)講演予稿集 1C6-54, p. 832, 2002年03月
    日本語, 口頭発表(一般)
  • 直鎖ポリマーを基材とした高親和性ベロ毒素阻害剤の開発               
    渡邊美帆; 西川喜代孝; 松岡浩司; 照沼大陽; 名取泰博
    日本薬学会第122回年会(千葉)講演要旨集 28PI-553, 2002年03月
    日本語, ポスター発表
  • N-アセチルラクトサミン誘導体の効率的調製法               
    大田和拓己; 松岡浩司; 西村紳一郎; 幡野 健; 照沼大陽
    日本化学会北海道支部2002年冬季研究発表会(札幌)講演予稿集 2B12, p. 84, 2002年02月
    日本語, 口頭発表(一般)
  • 機能性ポリシランの開発 –発光材料への応用–               
    八百板善幸; 幡野健; 松岡浩司; 石井礼仁; 鎌田憲彦; 照沼大陽
    ケイ素化学協会第6回ケイ素化学協会シンポジウム(仙台)講演要旨集, 2001年11月
    日本語, ポスター発表
  • 機能性カルボシロキサンデンドリマーの合成 –糖鎖導入法の検討–               
    土田隆樹; 幡野健; 松岡浩司; 照沼大陽; 吉武誠
    ケイ素化学協会第6回ケイ素化学協会シンポジウム(仙台)講演要旨集, 2001年11月
    日本語, ポスター発表
  • 新規パラジウム錯体担持カルボシランデンドリマーの合成と評価               
    阿部展久; 幡野健; 松岡浩司; 江角保明; 照沼大陽
    ケイ素化学協会第6回ケイ素化学協会シンポジウム(仙台)講演要旨集, 2001年11月
    日本語, ポスター発表
  • 新規両親媒性ポリシランの合成とそのLB膜化               
    森泉幸也; 石井礼仁; 幡野健; 松岡浩司; 鎌田憲彦; 照沼大陽
    ケイ素化学協会第6回ケイ素化学協会シンポジウム(仙台)講演要旨集, 2001年11月
    日本語, ポスター発表
  • オリゴシランの末端官能基化とその応用の関する研究               
    斉藤和久; 幡野健; 松岡浩司; 鎌田憲彦; 江角保明; 照沼大陽
    ケイ素化学協会第6回ケイ素化学協会シンポジウム(仙台)講演要旨集, 2001年11月
    日本語, ポスター発表
  • 可溶性ポリジフェニルシラン誘導体の合成と評価               
    頓所真司; 石井礼仁; 鎌田憲彦; 幡野健; 松岡浩司; 照沼大陽
    ケイ素化学協会第6回ケイ素化学協会シンポジウム(仙台)講演要旨集, 2001年11月
    日本語, ポスター発表
  • Preparation and Characterization of New Carbosilane Dendrimer Catalysts bearing Palladium Complexes for Heck Reaction               
    Abe, N.; Hatano, K.; Matsuoka, K.; Esumi, Y.; Terunuma, D.
    The 2nd International Dendrimer Symposium (Tokyo, Japan), October 14 – 17, 2001, PA28, p. 88, 2001年10月
    2001年10月 - 2001年10月, 英語, ポスター発表
  • Bioactive Glycodendrimers Using Carbosilane as the Core Scafforld               
    Matsuoka, K.; Esumi, Y.; Nishikawa, K.; Natori, Y.; Suzuki, Y.; Hatano, K.; Terunuma, D.; Kuzuhara, H.
    The 2nd International Dendrimer Symposium (Tokyo, Japan), October 14 – 17, 2001, PA10, p. 70, 2001年10月
    2001年10月 - 2001年10月, 英語, ポスター発表
  • 新規両親媒性ポリシランの合成とそのLB膜化               
    森泉幸也; 石井礼仁; 幡野健; 松岡浩司; 鎌田憲彦; 照沼大陽
    高分子学会第50回高分子討論会(早稲田)講演予稿集 IIIPd 012, 2001年09月
    日本語, ポスター発表
  • パラジウム錯体担持カルボシランデンドリマーの合成と評価               
    阿部展久; 幡野健; 松岡浩司; 照沼大陽
    高分子学会第50回高分子討論会(早稲田)講演予稿集 IIPh 008, 2001年09月
    日本語, ポスター発表
  • 可溶性ポリジフェニルシラン誘導体の合成と評価               
    頓所真司; 登坂健志; 石井礼仁; 鎌田憲彦; 幡野健; 松岡浩司; 照沼大陽
    高分子学会第50回高分子討論会(早稲田)講演予稿集 IIPd 056, 2001年09月
    日本語, ポスター発表
  • 糖鎖を基盤とした機能材料の合成研究               
    松岡浩司
    高分子学会第97回東海支部研究会(西浦)講演要旨集【招待講演】, 2001年08月, [招待有り]
    日本語, 口頭発表(招待・特別)
  • シアリルラクトース含有カルボシランデンドリマーの合成と抗インフルエンザウィルス活性               
    岡博之; 松岡浩司; 鈴木康夫; 江角保明; 照沼大陽
    日本糖質学会第22回日本糖質学会年会(静岡)講演要旨集 A3-12, p. 68, 2001年07月
    日本語, 口頭発表(一般)
  • グロボ3糖担持カルボシランデンドリマー群の合成とベロ毒素の中和能               
    松岡浩司; 照沼大陽; 葛原弘美
    大学連携型産業科学技術研究開発プロジェクト第3回グリコクラスター公開シンポジウム(札幌)講演要旨集 #03, p. 21, 2001年07月
    日本語, 口頭発表(一般)
  • クラウンエーテル担持カルボシランデンドリマーの合成               
    土田隆樹; 松岡浩司; 照沼大陽
    高分子学会第50回年次大会(大阪)講演予稿集 IIIPb 028, p. 296, 2001年05月
    日本語, ポスター発表
  • 光応答性基を有するカルボシランデンドリマーの合成とその物性 [III]               
    小山哲夫; 松岡浩司; 照沼大陽
    高分子学会第50回年次大会(大阪)講演予稿集 IIIPa 017, p. 290, 2001年05月
    日本語, ポスター発表
  • ベロ毒素を標的としたアフィニティークロマトグラフ担体の調製               
    松岡浩司; 宮川淳; 照沼大陽; 西川喜代孝; 名取泰博
    高分子学会第50回年次大会(大阪)講演予稿集 IIPf 140, p. 1002, 2001年05月
    日本語, ポスター発表
  • 側鎖にEu3+イオンを包接したクラウンエーテルを有するポリシランコポリマーの合成               
    八百板善幸; 登坂健志; 松岡浩司; 鎌田憲彦; 照沼大陽
    高分子学会第50回年次大会(大阪)講演予稿集 IIPd 006, p. 225, 2001年05月
    日本語, ポスター発表
  • シアリルラクトース含有カルボシランデンドリマーの構築を目的とした縮合法の検討               
    岡博之; 松岡浩司; 江角保明; 照沼大陽
    日本化学会第79回春季年会(神戸)講演予稿集 3F5 35, p. 939, 2001年03月
    日本語, 口頭発表(一般)
  • Design, Synthesis, and Biological Evaluation of Carbosilane Dendrimers Uniformly Functionalized with Bioactive Saccharide Sequence               
    Matsuoka, K.; Oka, H.; Tsuchida, T.; Nishikawa, K.; Natori, Y.; Esumi, Y.; Terunuma, D.; Kuzuhara, H.
    Pacifichem 2000 (Hawaii, U.S.A.), December 14 – 19, 2000, #776, 2000年12月
    2000年12月 - 2000年12月, 英語, ポスター発表
  • The Synthesis of Water-Soluble Polysilanes and their Application to Sol-Gel Glass Filing               
    Terunuma, D.; Yaoita, Y.; Matsuoka, K.; Sato, H.; Kamata, N.
    Pacifichem 2000 (Hawaii, U.S.A.), December 14 – 19, 2000, #959, 2000年12月
    2000年12月 - 2000年12月, 英語, ポスター発表
  • Development of a New Type of Shiga Toxin Neutralizer, Carbosilane Dendrimer, which Completely Rescues the Lethality of Shiga Toxin 2 in Mice               
    Nishikawa, K.; Matsuoka, K.; Okabe, N.; Mizuguchi, M.; Aoki, J.; Yamasaki, C.; Yamakawa, Y.; Nishijima, M.; Arai, H.; Terunuma, D.; Kuzuhara, H.; Natori, Y.
    4th International Symposium and Workshop on “SHIGA TOXIN (VEROTOXIN)-Producing ESCHERICA COLI Infections” (Kyoto, Japan), October 29 – November 2, 2000, #415, p. 180, 2000年11月
    2000年10月 - 2000年11月, 英語, ポスター発表
  • カルボシランデンドリマー・糖鎖複合材料 —ベロ毒素接着能に与えるデンドリマー構造の効果—               
    照沼大陽; 松岡浩司; 葛原弘美
    ケイ素化学協会第5回ケイ素化学協会シンポジウム(東大阪)講演要旨集 Topics 5, pp. 30-31, 2000年11月, [招待有り]
    日本語, 口頭発表(招待・特別)
  • カルボシランデンドリマーの構造とその液晶性               
    土田隆樹; 松岡浩司; 照沼大陽
    ケイ素化学協会第5回ケイ素化学協会シンポジウム(東大阪)講演要旨集 P32, p. 68, 2000年11月
    日本語, ポスター発表
  • 光応答性カルボシランデンドリマーの合成とその物性               
    小山哲夫; 松岡浩司; 照沼大陽
    ケイ素化学協会第5回ケイ素化学協会シンポジウム(東大阪)講演要旨集 P30, p. 66, 2000年11月
    日本語, ポスター発表
  • カルボシランデンドリマーの合成研究:病原性大腸菌O-157が産生するベロ毒素に対する中和剤               
    松岡浩司; 照沼大陽; 江角保明; 葛原弘美
    ケイ素化学協会第5回ケイ素化学協会シンポジウム(東大阪)講演要旨集 P27, p. 63, 2000年11月
    日本語, ポスター発表
  • カルボシランデンドリマーをコア骨格とする新規インフルエンザウィルス接着材料の合成研究               
    岡博之; 松岡浩司; 照沼大陽; 葛原弘美
    ケイ素化学協会第5回ケイ素化学協会シンポジウム(東大阪)講演要旨集 P22, p. 58, 2000年11月
    日本語, ポスター発表
  • 新規可溶性ポリジフェニルシラン類の合成               
    頓所真司; 佐藤弘基; 鎌田憲彦; 松岡浩司; 照沼大陽
    ケイ素化学協会第5回ケイ素化学協会シンポジウム(東大阪)講演要旨集 P3, p. 39, 2000年11月
    日本語, ポスター発表
  • ゾル-ゲルガラス中での水溶性ポリシランの光学特性,               
    八百板善幸; 佐藤弘基; 鎌田憲彦; 松岡浩司; 照沼大陽
    ケイ素化学協会第5回ケイ素化学協会シンポジウム(東大阪)講演要旨集 P1, p. 37, 2000年11月
    日本語, ポスター発表
  • 機能性糖鎖を担持したカルボシランデンドリマーの合成研究               
    松岡浩司; 照沼大陽; 江角保明; 葛原弘美
    有機合成化学協会第78回有機合成シンポジウム(京都)講演要旨集 2A-15, pp. 321-324, 2000年09月
    日本語, 口頭発表(一般)
  • Systematic Synthesis of Carbosilane Dendrimers Functionalized with the Globotriaosyl Moieties Having Neutralization Potency for Verotoxins               
    Matsuoka, K.; Terabatake, M.; Nishikawa, K.; Natori, Y.; Esumi, Y.; Terunuma, D.; Kuzuhara, H.
    20th International Carbohydrate Symposium (Hamburg, Germany), August 27 – September 1, 2000, B-056, p. 106, 2000年09月
    2000年08月 - 2000年09月, 英語, 口頭発表(一般)
  • Glyco-Silicon機能材料(X): 世代と形状の異なるグロボ3糖含有カルボシランデンドリマー類の合成とベロ毒素に対するそれらの中和活性能               
    松岡浩司; 寺畠未希子; 黒澤英弘; 西川喜代孝; 名取泰博; 江角保明; 照沼大陽; 葛原弘美
    日本糖質学会第21回日本糖質学会年会(名古屋)講演要旨集 A3-01, p. 48, 2000年07月
    日本語, 口頭発表(一般)
  • Glyco-Silicon機能材料(IX): シアリルラクトース含有カルボシランデンドリマーの合成研究               
    岡博之; 松岡浩司; 照沼大陽; 葛原弘美
    日本糖質学会第21回日本糖質学会年会(名古屋)講演要旨集 PII-01, p. 107, 2000年07月
    日本語, ポスター発表
  • 特定炭素上に水酸基を残したメチル化-CDの合成とそれらの包接能               
    松岡浩司; 白石暢子; 照沼大陽; 葛原弘美
    日本糖質学会第21回日本糖質学会年会(名古屋)講演要旨集 PI-11, p. 84, 2000年07月
    日本語, ポスター発表
  • ベロ毒素の中和活性能を有するグロボ3糖を均一に担持したカルボシランデンドリマー群の合成研究               
    松岡浩司; 照沼大陽; 葛原弘美
    大学連携型産業科学技術研究開発プロジェクト第2回グリコクラスター公開シンポジウム(札幌)講演要旨集 #04, 2000年07月, [招待有り]
    日本語, 口頭発表(一般)
  • Glyco-silicon機能材料(VIII):還元的アミノ化法によるカルボシランデンドリマーへの糖鎖の導入               
    松岡浩司; 黒澤英弘; 江角保明; 照沼大陽; 葛原弘美
    日本化学会第78回春季年会(船橋)講演予稿集 3D5 26, p. 827, 2000年03月
    日本語, 口頭発表(一般)
  • シアル酸のアジド誘導体の合成               
    岡博之; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会第78回春季年会(船橋)講演予稿集 3D5 25, p. 826, 2000年03月
    日本語, 口頭発表(一般)
  • クラウンエーテルを有するカルボシランデンドリマーの合成とイオン抽出能               
    照沼大陽; 中川淳; 松岡浩司; 葛原弘美
    高分子学会第48回高分子討論会(新潟)講演予稿集 IIPd 074, p. 2469-2470, 1999年10月
    日本語, ポスター発表
  • 光応答性基を有するカルボシランデンドリマーの合成とその物性(2)               
    小山哲夫; 照沼大陽; 松岡浩司; 葛原弘美
    高分子学会第48回高分子討論会(新潟)講演予稿集 IC 11, p. 1763-1764, 1999年10月
    日本語, 口頭発表(一般)
  • Glyco-silicon機能材料(VII):グロボ3糖を均一に結合させたカルボシランデンドリマーの合成とベロ毒素に対する中和活性               
    松岡浩司; 岡博之; 江角保明; 照沼大陽; 葛原弘美
    日本化学会第77回秋季年会(札幌)講演予稿集 1A4 03, p. 680, 1999年09月
    日本語, 口頭発表(一般)
  • 側鎖に光学活性な置換基を有する水溶性ポリシランの合成と評価               
    照沼大陽; 南雲公二; 鎌田憲彦; 松岡浩司; 葛原弘美
    電子情報通信学会有機エレクトロニクス研究会(東京) OME99-75, 1999年09月
    日本語, 口頭発表(一般)
  • Synthesis of Carbosilane Dendrimers Uniformly Functionalized with Carbohydrate Moieties of Globotriaosyl Ceramide as a Potential Drug for Neutralization of Microbacterial Toxin               
    Matsuoka, K.; Terabatake, M.; Umino, A.; Esumi, Y.; Terunuma, D.; Kuzuhara, H.
    XV International Symposium on Glycoconjugates (Tokyo, Japan), August 22 – 27, 1999, 4pP#475, S166, 1999年08月
    1999年08月 - 1999年08月, 英語, ポスター発表
  • Preparation and Characterization of Carbosilane Dendrimers Carrying Mesogens               
    Nishio, R.; Terunuma, D.; Aoki, Y.; Nohira, H.; Matsuoka, K.; Kuzuhara, H.
    The 12th International Symposium on Organosilicon Chemistry (Sendai, Japan), May 23 - 28, 1999, P150, p. 219, 1999年05月
    1999年05月 - 1999年05月, 英語, ポスター発表
  • 光応答性基を有するカルボシランデンドリマーの合成とその物性               
    小山哲夫; 照沼大陽; 加藤智則; 松岡浩司; 葛原美弘
    高分子学会第48回年次大会(京都)講演予稿集 IPg 129, p. 734, 1999年05月
    日本語, ポスター発表
  • シロキサンを主鎖とする側鎖型強誘電性液晶の合成               
    照沼大陽; 湯浅敦史; 青木良夫; 野平博之; 松岡浩司; 葛原弘美
    日本化学会第76回春季年会(横浜)講演予稿集 1E6 27, p. 1396, 1999年03月
    日本語, 口頭発表(一般)
  • 2糖トレハロースを出発物としたL-イズロン酸の新規合成法               
    比能洋; 黒澤英弘; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会第76回春季年会(横浜)講演予稿集 2A1 02, p. 681, 1999年03月
    日本語, 口頭発表(一般)
  • 酵素と合成を併用したキトビオースの位置選択的修飾               
    松沢克明; 金子哲; 徳安健; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会第76回春季年会(横浜)講演予稿集 2A1 01, p. 681, 1999年03月
    日本語, 口頭発表(一般)
  • Glyco-silicon機能材料(VI):12個のグロボ3糖で修飾されたカルボシランデンドリマーの合成               
    寺畠未希子; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会第76回春季年会(横浜)講演予稿集 1A1 36, p. 680, 1999年03月
    日本語, 口頭発表(一般)
  • Glyco-silicon機能材料(V):第1世代カルボシランデンドリマーの合成と12個のシクロデキストリンによる修飾               
    齋藤洋祐; 松岡浩司; 江角保明; 照沼大陽; 葛原弘美
    日本化学会第76回春季年会(横浜)講演予稿集 1A1 37, p. 680, 1999年03月
    日本語, 口頭発表(一般)
  • Glyco-silicon機能材料(IV):アレイ型カルボシランデンドリマーの合成と各種単糖類との縮合               
    黒澤英弘; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会第76回春季年会(横浜)講演予稿集 1A1 36, p. 680, 1999年03月
    日本語, 口頭発表(一般)
  • 光学活性な置換基を有するカルボシランデンドリマー液晶の合成               
    西尾玲; 照沼大陽; 松岡浩司; 葛原弘美; 青木良夫; 野平博之
    ケイ素化学協会第3回ケイ素化学協会シンポジウム,講演要旨集, 1998年11月
    日本語, ポスター発表
  • 光学活性基を有するポリシラン類の合成               
    南雲公二; 太田洋介; 照沼大陽; 天野裕貴; 鎌田憲彦; 松岡浩司; 葛原弘美
    ケイ素化学協会第3回ケイ素化学協会シンポジウム 講演要旨集, 1998年11月
    日本語, ポスター発表
  • セロビオースより誘導したグリカールモノマーの合成とその重合反応               
    松岡浩司; 小川裕治; 比能洋; 照沼大陽; 葛原弘美
    日本糖質学会第20回糖質シンポジウム(札幌)講演要旨集 A2-01, p. 39, 1998年07月
    日本語, ポスター発表
  • 新規LCデンドリマーの合成とその評価               
    西尾玲; 照沼大陽; 加藤智則; 小澤尚史; 松岡浩司; 葛原弘美; 青木良夫; 野平博之
    日本化学会第2回液晶化学研究会シンポジウム, 1998年06月
    日本語, 口頭発表(一般)
  • 側鎖に光学活性部位を有するポリヘキシルフェニルシラン(PHPS)誘導体の合成とその評価               
    南雲公二; 照沼大陽; 松岡浩司; 葛原弘美; 鎌田憲彦
    高分子学会第47回年次大会(京都)講演予稿集 IIIPd 090, 1998年05月
    日本語, ポスター発表
  • 光学活性部位として(-)-mentholを有するポリシランの合成               
    天野裕貴; 照沼大陽; 松岡浩司; 葛原弘美; 鎌田憲彦
    高分子学会第47回年次大会(京都)講演予稿集 IIIPc 089, 1998年05月
    日本語, ポスター発表
  • 機能性基を有するカルボシランデンドリマーの合成               
    照沼大陽; 加藤智則; 松岡浩司; 葛原弘美
    高分子学会第47回年次大会(京都)講演予稿集 IIIPd 088, 1998年05月
    日本語, ポスター発表
  • 液晶分子を有する新規カルボシランデンドリマーの合成               
    西尾玲; 照沼大陽; 加藤智則; 松岡浩司; 葛原弘美; 青木良夫; 野平博之
    高分子学会第47回年次大会(京都)講演予稿集 IPf 116, 1998年05月
    日本語, ポスター発表
  • 側鎖に光学活性部位を有するポリシラン誘導体の合成と評価               
    照沼大陽; 南雲公二; 松岡浩司; 葛原弘美
    有機合成化学協会第35回有機合成化学協会関東支部シンポジウム(埼玉)講演予稿集, 1998年05月
    日本語, 口頭発表(一般)
  • 光学活性基を側鎖に有するポリシランの合成とその構造               
    照沼大陽; 南雲公二; 天野裕貴; 鎌田憲彦; 松岡浩司; 葛原弘美
    電子情報通信学会有機エレクトロニクス研究会(東京) OME98-2, 1998年05月
    日本語, 口頭発表(一般)
  • Glyco-silicon機能材料(III):カルボシランデンドリマー最小単位へのラクトース及びグロボ3糖の導入反応               
    海野篤; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会第74回春季年会(京田辺)講演予稿集 4G2 33, p. 1264, 1998年03月
    日本語, 口頭発表(一般)
  • トレハロースを結合部位とした、新規なシクロデキストリンダイマーの合成と包接能評価               
    齋藤洋祐; 松岡浩司; 照沼大陽; 葛原
    日本化学会第74回春季年会(京田辺)講演予稿集 4G2 02, p. 1258, 1998年03月
    日本語, 口頭発表(一般)
  • セロビオースのグリカール誘導体をモノマーとする重合反応               
    小川裕治; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会第74回春季年会(京田辺)講演予稿集 1E6 29, p. 1100, 1998年03月
    日本語, 口頭発表(一般)
  • キチンの酵素分解によるキトビオース調製法の効率化と、キトビオースの化学変換               
    松沢克明; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会第74回春季年会(京田辺)講演予稿集 1E6 28, p. 1100, 1998年03月
    日本語, 口頭発表(一般)
  • トレハロースのL-イドース含有2糖への変換反応               
    比能洋; 黒澤英弘; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会第74回春季年会(京田辺)講演予稿集 1E6 27, p. 1100, 1998年03月
    日本語, 口頭発表(一般)
  • 側鎖に光学活性部位を有するポリヘキシルフェニルシラン(PHPS)誘導体の合成とその評価               
    照沼大陽; 南雲公二; 鎌田憲彦; 松岡浩司; 葛原弘美
    第7回有機ポリシラン・フォーラム(浦和)講演予稿集 1, pp. 1-4, 1998年01月
    日本語, 口頭発表(一般)
  • Preparation of Amphiphilic Polysilanes Having a Chiral Pendant Ammonium Moiety               
    Terunuma, D.; Nagumo, K.; Matsuoka, K.; Kuzuhara, H.
    ケイ素系高分子材料国際シンポジウム (Chiyoda, Tokyo), June 23-24, 1997, 1997年10月
    1997年10月 - 1997年10月, 英語, ポスター発表
  • 両親媒性キトヘプタオース誘導体の合成               
    比能洋; 海野篤; 松岡浩司; 照沼大陽; 葛原弘美
    日本糖質学会第19回糖質シンポジウム(西宮)講演要旨集 A3-11, p. 56, 1997年08月
    日本語, 口頭発表(一般)
  • 液体アンモニアを溶媒とするシクロデキストリン包接不斉還元反応               
    松岡浩司; 齋藤洋祐; 高橋寛幸; 照沼大陽; 葛原弘美
    日本糖質学会第19回糖質シンポジウム(西宮)講演要旨集 D-14, p. 97, 1997年08月
    日本語, 口頭発表(一般)
  • Preparation of Amphiphilic Polysilanes;Having a Chiral Pendan;Ammonium Moiety               
    Terunuma, D.; Nagumo, K.; Matsuoka, K.; Kuzuhara, H.
    ケイ素系高分子材料国際シンポジウム (Chiyoda, Tokyo), June 23-24, 1997, 1997年06月
    1997年06月 - 1997年06月, 日本語, ポスター発表
  • 分子集合能を持つキトビオース誘導体の合成               
    比能洋; 海野篤; 松岡浩司; 照沼大陽; 葛原弘美
    日本キチン・キトサン学会第11回キチン・キトサンシンポジウム(静岡)講演予稿集, 1997年06月
    日本語, 口頭発表(一般)
  • カルボシラン骨格を有する傾斜型デンドリマーの合成               
    照沼大陽; 西尾玲; 加藤智則; 松岡浩司; 葛原弘美
    高分子学会第46回年次大会(目黒)講演予稿集 IIIPd 016, p. 272, 1997年05月
    日本語, ポスター発表
  • 機能性Glyco-silicon複合材料II:アレイ型有機ケイ素骨格上へのシクロデキストリンの固定化               
    松岡浩司; 萩原知春; 照沼大陽; 葛原弘美; 江角保明
    高分子学会第46回年次大会(目黒)講演予稿集 IIF 28, p. 475, 1997年05月
    日本語, 口頭発表(一般)
  • 両親媒性キトオリゴ糖誘導体の合成II 2本の疎水性長鎖を結合した3糖、5糖、7糖の合成               
    比能洋; 海野篤; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会第72回春季年会(豊島)講演予稿集 4G3 32, p. 1021, 1997年03月
    日本語, 口頭発表(一般)
  • 両親媒性キトオリゴ糖誘導体の合成I 長鎖アシルアミノ基を活用したグリコシル化反応               
    海野篤; 比能洋; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会第72回春季年会(豊島)講演予稿集 4G3 31, p. 1021, 1997年03月
    日本語, 口頭発表(一般)
  • リチウムナフタレニドに対するフェニルチオセロビオシド誘導体の特異な反応性               
    小川祐治; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会第72回春季年会(豊島)講演予稿集 4G3 13, p. 1018, 1997年03月
    日本語, 口頭発表(一般)
  • ケイ素を分岐点とする機能性デンドリマーの合成I—シクロデキストリンの固定化と包接能               
    松岡浩司; 萩原知春; 照沼大陽; 葛原弘美
    日本化学会第72回春季年会(豊島)講演予稿集 4B3 15, p. 689, 1997年03月
    日本語, 口頭発表(一般)
  • 液晶分子を有するデンドリマー類の合成               
    照沼大陽; 加藤智則; 西尾玲; 松岡浩司; 葛原弘美; 青木良夫; 野平博之
    日本化学会第72回春季年会(豊島)講演予稿集 2PB0 29, 1997年03月
    日本語, 口頭発表(一般)
  • 官能基を有するカルボシランデンドリマー               
    加藤智則; 西尾玲; 照沼大陽; 松岡浩司; 葛原弘美
    ケイ素化学協会第1回ケイ素化学協会シンポジウム(筑波)講演予稿集, 1996年11月
    日本語, ポスター発表
  • 機能性基を規則的に配列したシロキサン鎖の合成               
    長谷川準; 照沼大陽; 松岡浩司; 葛原弘美
    ケイ素化学協会第1回ケイ素化学協会シンポジウム(筑波)講演予稿集, 1996年11月
    日本語, ポスター発表
  • ミセル形成能を持つ生理活性キトオリゴ糖誘導体の合成研究               
    比能洋; 海野篤; 松岡浩司; 照沼大陽; 葛原弘美
    日本糖質学会第18回糖質シンポジウム(目黒)講演要旨集 P-10, p. 141, 1996年08月
    日本語, ポスター発表
  • 側鎖に官能基を導入したシロキサンポリマーの合成               
    照沼大陽; 長谷川準; 松岡浩司; 葛原弘美
    高分子学会第45回年次大会(名古屋)講演予稿集 IPc 001, 1996年05月
    日本語, 口頭発表(一般)
  • キトオリゴ糖ミセルの合成研究               
    比能洋; 海野篤; 松岡浩司; 照沼大陽; 葛原弘美
    日本化学会第70回春季年会(渋谷)講演予稿集 4C2 45, p. 656, 1996年03月
    日本語, 口頭発表(一般)
  • 抗腫瘍、抗ウィルス性天然物マイカラミドAの合成研究               
    中田忠; 福井英人; 松倉弘子; 中川忠清; 松岡浩司
    日本薬学会第21回反応と合成の進歩シンポジウム(京都)講演要旨集 , pp. 204-208, 1995年12月
    日本語
  • Ceramide Glycanase Assay by Fluorescence Quenching and Energy Transfer Using a Bi-Fluorescence-Labelled Lactoside               
    Matsuoka, K.; Kimura, N.; Nishimura, S.-I.; Lee, Y. C.
    XIIIth International Symposium on Glycoconjugates (Seattle, USA), August 20 – 26, 1995, p. 410, 1995年08月
    1995年08月 - 1995年08月, 英語, ポスター発表
  • アミラーゼの新しい合成基質: 二重蛍光プローブを有するマルトオリゴ糖誘導体の調製               
    木村直紀; 松岡浩司; 西村紳一郎; Yuan C. Lee
    日本糖質学会第17回糖質シンポジウム(京都)講演要旨集 C-8, p. 165, 1995年07月
    日本語, 口頭発表(一般)
  • シアル酸キャップ構造を持つシクロデキストリンの合成と機能               
    松岡浩司; 松田匡雄; 西村紳一郎
    高分子学会第44回年次大会(横浜)講演予稿集 IPc 119, p. 624, 1995年05月
    日本語, 口頭発表(一般)
  • 二種類の蛍光プローブを有するラクトース誘導体の合成と評価: セラミドグリカナーゼの便利な基質として               
    松岡浩司; Yuan C. Lee; 西村紳一郎
    日本化学会第69回春季年会(京都)講演予稿集 3D334, 1995年03月
    日本語, 口頭発表(一般)
  • 糖脂質分解酵素により加水分解される新規なラクトース誘導体の合成と基質としての評価‥‥‥二種類の異なる蛍光プローブによる蛍光の消光とエネルギー移動を利用して               
    松岡浩司; Yuan C. Lee; 西村紳一郎
    日本化学会北海道支部1995年冬季研究発表会(札幌)講演要旨集 1A26, p. 26, 1995年02月
    日本語, 口頭発表(一般)
  • 糖タンパク質モデルの研究 [13]: ラクトースおよびN-アセチルラクトサミン結合性レクチンの新しいリガンドの分子設計               
    松岡浩司; 古池哲也; 西村紳一郎
    日本化学会第68回秋季年会(名古屋)講演予稿集 3C623, p. 300, 1994年10月
    日本語, 口頭発表(一般)
  • Synthetic Glycopolymer Related to Chitooligosaccharides: Novel Cluster Ligands for Wheat Germ Agglutinin               
    Nishimura, S.-I.; Matsuoka, K.; Furuike, T.; Nagata, K.; Nishi, N.; Tokura. S.
    6th International Conference on Chitin and Chitosan (Gdynia, Poland), August 16 - 19, 1994, p. 9, 1994年08月
    1994年08月 - 1994年08月, 英語, 口頭発表(一般)
  • 糖鎖合成のための新しい高分子担体の分子設計               
    西村紳一郎; 松岡浩司; Yuan C. Lee
    高分子学会第43回年次大会(名古屋)講演予稿集 I-9-12, p. 590, 1994年05月
    日本語, 口頭発表(一般)
  • 糖タンパク質モデルの研究 (10): ガラクトース転移酵素およびトランスシアリダーゼを用いた糖質高分子の調製               
    松岡浩司; 西村紳一郎; Kyung Bok Lee; Yuan C. Lee
    高分子学会第43回年次大会(名古屋)講演予稿集 I-9-10, p. 588, 1994年05月
    日本語, 口頭発表(一般)
  • 糖タンパク質モデルの研究;クラスター型モデル高分子とレクチンの相互作用               
    古池哲也; 西則雄; 戸倉清一; 松岡浩司; 永田謙二; 西村紳一郎
    高分子学会第43回年次大会(名古屋)講演予稿集 I-9-09, p. 587, 1994年05月
    日本語, 口頭発表(一般)
  • Fluorescent Derivatives of Glycopeptides, Oligosaccharides, and Glycosides               
    Lee, Yuan. C.; Rice, Kevin G.; Lee, Kyung Bok; Matsuoka, Koji; Lee, Reiko T.
    Keystone Symposia (Colorado USA), March 19 - 26, 1994, (1994.3)., 1994年03月
    1994年03月 - 1994年03月, 英語, 口頭発表(一般)
  • 癌関連糖鎖抗原を含む複合糖質モデルの合成               
    西村紳一郎; 松岡浩司; 古池哲也; 村山定生; 栗田恵輔
    日本糖質学会第14回糖質シンポジウム(東京), 1992年07月
    日本語, 口頭発表(一般)
  • Synthetic Studies on Glycoconjugate Models Having Pendant Oligosaccharides Related to Tumor Associated Antigen               
    Nishimura, S.-I.; Matsuoka, K.; Furuike, T.; Murayama, S.; Nagami, K.; Ishii, S.; Kurita; K.; Kuzuhara, H.
    XVIth International Carbohydrate Symposium (Paris, France), 1992年07月
    1992年07月 - 1992年07月, 英語, ポスター発表
  • 糖タンパク質モデルの基礎的研究 [VII]---高機能性スペーサーを利用した糖鎖の高次組織化               
    西村紳一郎; 松岡浩司; 古池哲也; 丸山健治; 石井茂; 栗田恵輔
    高分子学会第41回年次大会(横浜), 1992年05月
    日本語, 口頭発表(一般)
  • 糖タンパク質モデルの基礎的---癌関連糖鎖抗原を含む人工複合糖質の分子設計               
    西村紳一郎; 松岡浩司; 古池哲也; 丸山健治; 石井茂; 栗田恵輔; 持田恵子
    日本化学会第62回秋季年会(札幌), 1991年09月
    日本語, 口頭発表(一般)
  • 複合糖質モデルの研究---ラクトサミン関連オリゴ糖を含むモデル高分子の合成と利用               
    西村紳一郎; 松岡浩司; 古池哲也; 石井茂; 栗田恵輔; 持田恵子
    日本糖質学会第13回糖質シンポジウム(大阪), 1991年07月
    日本語, 口頭発表(一般)
  • Design, Syntheses;Properties of Novel;Synthetic Glycoconjugates               
    Nishimura, S.-I.; Matsuoka, K.; Furuike, T.; Nagami, K.; Ishii, S.; Kurita; K.; Nishimura, K. M.
    XIth International Symposium on Glycoconjugates (Toronto, Canada), 1991年07月
    1991年06月 - 1991年07月, 英語, ポスター発表
  • 細胞外マトリックスモデルの研究;ヒアルロン酸の基本構造を含む高分子の分子設計               
    西村紳一郎; 松岡浩司; 石井茂; 栗田恵輔
    高分子学会第40回年次大会(京都), 1991年06月
    日本語, 口頭発表(一般)
  • A Simple Method for the Preparation of Pseudo-Glycoproteins Containing Pendant N-Acetyl-D-glucosamine;and N.;N’-Diacetylchitobiose               
    Nishimura; S.-I.; Matsuoka; Kurita, K.
    IUPAC International Symposium on Speciality Polymers (Singapore, Singapore), 1990年11月
    1990年11月 - 1990年11月, 英語, ポスター発表
  • 糖タンパク質モデルの合成と性質に関する基礎的研究 [IV] ---種々のオリゴ糖を含む擬似複合糖質の合成               
    西村紳一郎; 松岡浩司; 栗田恵輔
    高分子学会第39回高分子討論会(名古屋), 1990年10月
    日本語, 口頭発表(一般)
  • Glycoprotein Models from N,N’-Diacetylchitobiose and the Related Oligosaccharides               
    Nishimura, S.-I.; Matsuoka, K.; Furuike, T.; Kurita, K.
    Int. Symp. on Chitin Derivatives in Life Science (Sapporo, Japan), 1990年10月
    1990年10月 - 1990年10月, 英語, ポスター発表
  • 糖タンパク質モデルの基礎的研究 (3)---N-アセチルラクトサミンおよび関連オリゴ糖を側鎖に含む高分子の合成               
    西村紳一郎; 松岡浩司; 古池哲也; 栗田恵輔
    日本化学会第60回秋季年会(広島), 1990年10月
    日本語, 口頭発表(一般)
  • 糖タンパタ質モデルの分子設計---細胞間相互作用に関連するオリゴ糖を含む人工複合糖質の合成研究               
    西村紳一郎; 松岡浩司; 永見憲; 栗田恵輔
    日本化学会第60回秋季年会(広島), 1990年10月
    日本語, 口頭発表(一般)
  • 糖タンパク質モデルの合成と性質に関する基礎的研究 [II]               
    西村紳一郎; 松岡浩司; 栗田恵輔
    高分子学会第39回年次大会(京都), 1990年05月
    日本語, 口頭発表(一般)
  • 糖タンパク質モデルの合成と性質に関する基礎的研究 [I]               
    西村紳一郎; 松岡浩司; 栗田恵輔
    高分子学会第39回年次大会(京都), 1990年05月
    日本語, 口頭発表(一般)
  • 複合糖質の研究               
    西村紳一郎; 松岡浩司; 栗田恵輔; 葛原弘美
    キチン・キトサン研究会第4回キチン・キトサンシンポジウム(京都), 1990年05月
    日本語, 口頭発表(一般)
■ 担当経験のある科目_授業
  • 2019年10月 - 現在
    高分子化学II, 埼玉大学
  • 機能分子合成特論, 埼玉大学大学院
  • 糖鎖工学特論, 埼玉大学大学院
  • 有機化学I, 埼玉大学
  • 有機機能材料, 埼玉大学
  • 基礎化学I, 埼玉大学
  • 高分子科学, 埼玉大学
  • 確率統計学, 埼玉大学
  • 材料有機化学, 埼玉大学
  • 構造解析I, 埼玉大学
■ 論文指導
  • 2008, 学士課程, 指導学生数計:4, 指導学生数(内留学生):0
  • 2009, 学士課程, 指導学生数計:4, 指導学生数(内留学生):0
  • 2010, 学士課程, 指導学生数計:5, 指導学生数(内留学生):0
  • 2011, 学士課程, 指導学生数計:5, 指導学生数(内留学生):0
  • 2012, 学士課程, 指導学生数計:4, 指導学生数(内留学生):0
  • 2008, 博士前期(専門職学位)課程, 指導学生数計:2, 指導学生数(内留学生):0
  • 2009, 博士前期(専門職学位)課程, 指導学生数計:4, 指導学生数(内留学生):0
  • 2010, 博士前期(専門職学位)課程, 指導学生数計:6, 指導学生数(内留学生):0
  • 2011, 博士前期(専門職学位)課程, 指導学生数計:8, 指導学生数(内留学生):0
  • 2012, 博士前期(専門職学位)課程, 指導学生数計:8, 指導学生数(内留学生):0
  • 2008, 博士後期課程, 指導学生数計:3, 指導学生数(内留学生):1
  • 2009, 博士後期課程, 指導学生数計:3, 指導学生数(内留学生):1
  • 2010, 博士後期課程, 指導学生数計:3, 指導学生数(内留学生):1
  • 2011, 博士後期課程, 指導学生数計:4, 指導学生数(内留学生):1
  • 2012, 博士後期課程, 指導学生数計:2, 指導学生数(内留学生):0
  • 2008, 研究生, 指導学生数計:1, 指導学生数(内留学生):0
  • 2012, 特別研究生, 指導学生数計:1, 指導学生数(内留学生):1
■ 所属学協会
  • FCCA
  • 日本糖質学会
  • アメリカ化学会
  • 有機合成化学協会
  • 高分子学会
  • 日本化学会
■ 共同研究・競争的資金等の研究課題
  • 糖鎖クラスターによる腫瘍関連マクロファージの高感度検出               
    日本学術振興会, 科学研究費助成事業, 基盤研究(B), 2024年04月 - 2027年03月
    松岡浩司; 松下隆彦; 小山哲夫; 熊倉嘉貴, 埼玉大学
    課題番号:24K02391
  • 糖鎖還元法を用いた病原体検出金ナノ微粒子の大量合成技術               
    日本学術振興会, 科学研究費助成事業, 挑戦的萌芽研究, 2016年04月01日 - 2019年03月31日
    小山 哲夫; 松岡 浩司, 埼玉大学
    配分額(総額):3770000, 配分額(直接経費):2900000, 配分額(間接経費):870000
    本課題は、糖鎖誘導体を用いて塩化金酸水溶液を還元し、当該糖鎖誘導体が表面に導入された金ナノ微粒子を合成することを目的とした。糖鎖誘導体はベロ毒素と選択的に結合するグロボ3糖を用い、金ナノ微粒子が生成することを確認した。
    本研究本来の目的は『病原体の存在が目に見える形でわかる』微粒子の構築であったが、色調変化が想定よりも乏しいことが判明した。同じ糖鎖誘導体を原料としたポリマーを合成し、金ナノ微粒子と共に溶液中に分散させた結果、溶液中で色調変化が明瞭に現れることが明らかとなった。
    当初の想定と異なった結果となったが、同様の成果を得ることが出来た。
    課題番号:16K13621
  • C型肝炎ウイルス糖ペプチドを用いた中和抗体作製と、新規診断技術への応用               
    日本学術振興会, 科学研究費助成事業, 基盤研究(B), 2013年04月01日 - 2017年03月31日
    清水 弘樹; 奥田 徹哉; 鈴木 哲朗; 松岡 浩司; 松尾 一郎, 国立研究開発法人産業技術総合研究所
    配分額(総額):18980000, 配分額(直接経費):14600000, 配分額(間接経費):4380000
    E2糖タンパクのアミノ酸配列は、C型肝炎ウイルス(HCV)株間で保存性が小さく多様性に富んでいるため,この部分を抗原とする抗体ができれば,株間に依存しないHCV迅速検出系の開発や有用なHCV中和抗体の創出が期待できる。本研究では,E2の中でもアミノ酸配列の保存性が高い糖鎖付加領域に着目し,糖ペプチド部を認識する抗体の開発を目指した。
    我々の有する糖鎖を抗原とした免疫法用いた抗原キャリアを導入した5糖10残基ペプチド体の合成を進めたところ非常に困難をみたが,最終的にはマイクロ波利用固相法により達成できた。そして、この抗原を使って免疫を進め、抗体の取得研究を進めた。
    課題番号:25293134
  • 病原性大腸菌O157感染症治療薬開発のための基盤研究               
    日本学術振興会, 科学研究費助成事業, 基盤研究(B), 2005年 - 2007年
    名取 泰博; 西川 喜代孝; 松岡 浩司, 国立国際医療センター(研究所)
    配分額(総額):15990000, 配分額(直接経費):14700000, 配分額(間接経費):1290000
    病原性大腸菌O157の主たる病原因子であるベロ毒素は、細胞表面に存在する糖脂質Gb3のグロボ3糖と結合し、その毒性を発揮する。我々はこれまで、分子内に複数のグロボ3糖を有するカルボシランデンドリマー及びアクリルアミド(AA)ポリマーを合成し、これらが試験管内及び動物個体内でベロ毒素と強く結合し、その毒性を中和することを報告した。本研究では、1型及び2型ベロ毒素(Stx1及びStx2)の中和に最適なデンドリマー構造を調べ、デンドリマーによるベロ毒素の中和にはダンベル型のデンドリマー構造でその両端に糖鎖クラスターが存在すること、両クラスター間の距離は1.1nm以上であること、毒素との結合には計4個のグロボ3糖で充分だが、血中での中和には最低計6個(片方のクラスターに3個)以上の糖鎖があること、クラスター内の糖鎖は同一ケイ素に結合していること、が必要であることを明らかにした。またこのデンドリマー骨格のダンベル型構造は試験管内における中和活性には必要なく、個体内において毒素と複合体を形成した後にマクロファージによって処理されるのに必要であることがわかった。さらにデンドリマーのコア部分とグロボ3糖の間のスペーサーの長さ及び疎水性の異なる化合物を作成し、毒素結合活性との関係を調べた結果、最初に作成したデンドリマー構造が最も中和活性が強いことがわかった。一方、AAポリマーについてポリアクリルアミド骨格とグロボ3糖との間のスペーサーの長さを変えたポリマーを作製し、ベロ毒素との結合活性を調べたところ、同様に初期のポリマーが最も強い活性を示すことがわかった。以上の結果から、Stx1とStx2の毒性中和に最適な構造が明らかになり、O157感染症治療薬開発の基盤が得られたと考える。
    課題番号:17390038
  • ベロ毒素を標的とした新規糖鎖クラスター型治療薬の合成研究               
    日本学術振興会, 科学研究費助成事業, 若手研究(B), 2003年 - 2004年
    松岡 浩司, 埼玉大学
    配分額(総額):3600000, 配分額(直接経費):3600000
    Vero毒素産生性大腸菌(Verotoxin-producing Escherichia coli ; VTEC)が産生するベロ毒素(VT)は、毒性を発揮するAサブユニットと細胞に接着する5つのBサブユニットから構成されるAB_5型の毒素である。さらに、糖鎖結合部位は、Bサブユニット1個あたり3箇所存在するため、全体で15箇所存在することも知られている。この多価の結合部位を有するVTsは、まずBサブユニットが、宿主細胞表層に存在するグロボトリオシルセラミド(Gb3)を特異的に認識、結合後、エンドサイトーシスによりAサブユニットがその細胞に侵入し、細胞の蛋白質合成を阻害する。すなわち、この感染初期段階となる毒素と宿主細胞との結合を、阻害あるいは中和することが可能となれば、感染やさらなる伝染の進行を未然に防ぐことができると考えられる。これまでに我々は、この過程を効果的に阻害する化合物群の合成を目的として、カルボシランデンドリマーの合成と活性評価に関する基礎的研究を行い、多価型化合物の有効性を確認してきた。その化合物群は、合成世代により分子量と表層官能基数が厳密に制御できるため、グロボ3糖構造(Galα1-4Ga1β1-4Glcβ1-)を規則的に被覆することが可能であった。また、これらは2種類のベロ毒素双方に対して、化合物群の合成世代や形状に応じた興味深い活性を示した。そこで、本研究では、その方法論を発展させ、以下の目的の達成を目指した。
    ・生分解性が期待できる糖アルコール型の多価コア分子を合成し、その表層上におけるグロボ3糖間の距離やコア分子に起因するトポロジーの制御を検討した。
    ・脂溶性部位を導入した糖脂質モデルとして、新規な糖脂質型糖鎖クラスターの合成に展開を試みた。
    ・この方法論を種々のAB_5型の毒素群に幅広く展開することにより、効率的な毒素中和剤あるいは阻害剤の開発の可能性を検討した。
    課題番号:15750077
  • インフルエンザウィルスを標的としたシアリル糖鎖含有ケイ素デンドリマーの合成研究               
    日本学術振興会, 科学研究費助成事業, 奨励研究(A), 2000年 - 2001年
    松岡 浩司, 埼玉大学
    配分額(総額):2200000, 配分額(直接経費):2200000
    インフルエンザウィルスは、宿主のシアル酸を含む糖鎖を受容体として認識し特異的に結合するヘマグルチニンタンパク質と自らの受容体を破壊するシアリダーゼを併せもつ極めてユニークなウィルスである。このウィルスによる感染は、3量体として分布しているヘマグルチニンによる宿主のシアリル化糖鎖への結合によって引き起こされる。すなわち、この初期段階のヘマグルチニンと宿主細胞との結合を効果的に阻害する化合物が存在するれば、未然に感染を阻止できると期待した。本研究において、目的とした化合物は、上述の多価型受容体に効果的に結合することが期待できる表層にシアリルラクトースを有したデンドリマー型の化合物群を選定し、以下のことを中心に合成と評価を行った。
    ★糖鎖構造を担持するためのコアとなる有機ケイ素デンドリマーを世代と形状に着目して系統的に合成した。(投稿準備中)
    ★これまで我々が利用してきた液体アンモニア中でのワンポット結合反応が、種々の官能基を有する単糖由来の糖鎖誘導体と有機ケイ素デンドリマーとの結合反応についても展開可能であることを見出した。(Carbohydrate Res.誌に掲載済み)
    ★シアリルラクトース誘導体を化学合成し、新規な結合法によりデンドリマーコアへの導入を行なった。(Tetrahedron Lett.誌に掲載済み)
    我々が合成した化合物は、糖鎖の個数が増えるに従い抗インフルエンザウィルス活性が高まる結果を示し、これまで極めて合成例の少ない正確な分子量を有する多価型糖鎖リガンドの有効性を示した。
    課題番号:12750754
  • -               
    競争的資金
  • -               
    競争的資金
■ 産業財産権
  • 抗ミッドカインモノクローナル抗体及びそれを用いた免疫学的測定キット               
    松岡 浩司; 松下 隆彦; 幡野 健; 根本 直人; 新井 秀直; 野村 博, 特許権
    J-Global ID:201803019459032558
  • 水溶性ポルフィリン誘導体とそれらの製造方法               
    松岡 浩司; 石丸 雄大; 鈴木 美穂; 幡野 健, 特許権
    特許番号・登録番号:特許第6281901号
    J-Global ID:201803019434357240
  • ミッドカイン結合性ペプチドアプタマーおよびその使用               
    松岡 浩司; 根本 直人; 新井 秀直, 特許権
    J-Global ID:201703015239735172
  • 蛍光増感型物質によるウイルス、微生物を検出する方法               
    幡野 健; 村松 洋亮; 古川 剛; 松岡 浩司, 特許権
    J-Global ID:201603005354650307
  • 非晶質炭素膜への機能性材料の固定方法               
    平塚 傑工; 中森 秀樹; 松岡 浩司; 森田 眞史, 特許権
    特許番号・登録番号:特許第5935027号
    J-Global ID:201603016412069778
  • 水溶性ポルフィリン誘導体とそれらの製造方法               
    松岡 浩司; 石丸 雄大; 鈴木 美穂; 幡野 健, 特許権
    J-Global ID:201503008085044324
  • ダブルビオチンアンカー型リガンド固定化分子               
    松岡 浩司; 土渕 晃司; 幡野 健, 特許権
    特許番号・登録番号:特許第5717281号
    J-Global ID:201503008573213878
  • FRETを利用した酵素活性測定基質及びその製造方法               
    松岡 浩司; 荒井 啓克; 岡 博之; 幡野 健, 特許権
    特許番号・登録番号:特許第5697129号
    J-Global ID:201503078612594580
  • 糖鎖担持デンドリマーからなる標的選択的薬剤放出担体               
    相澤 宏明; 本庄 寿壮; 幡野 健; 松岡 浩司; 照沼 大陽, 特許権
    特許番号・登録番号:特許第5629888号
    J-Global ID:201403067017448644
  • 発光の色調変化による複数微生物の同時検出方法               
    幡野 健; 森 祥太; 佐伯 整; 照沼 大陽; 松岡 浩司, 特許権
    特許番号・登録番号:特許第5605542号
    J-Global ID:201403013123651731
  • フコシルキトビオース誘導体の製造方法               
    松岡 浩司; 照沼 大陽; 幡野 健; 山口 大希, 特許権
    特許番号・登録番号:特許第5605541号
    J-Global ID:201403012616943425
  • 金含有物への糖鎖の導入法               
    小山 哲夫; 松岡 浩司, 特許権
    特許番号・登録番号:特許第5597903号
    J-Global ID:201403006841096707
  • チオシアロシド型オリゴ糖を含む糖鎖デンドリマーの製造方法及びその利用               
    坂本 純一; 松岡 浩司; 照沼 大陽; 幡野 健; 鈴木 康夫, 特許権
    特許番号・登録番号:特許第5481731号
    J-Global ID:201403077657382424
  • シアル酸誘導体の製造方法とインフルエンザウィルス阻害剤としての利用               
    鈴木 香織; 坂本 純一; 松岡 浩司; 照沼 大陽; 幡野 健; 鈴木 康夫, 特許権
    特許番号・登録番号:特許第5327839号
    J-Global ID:201403003074223170
  • シアリルα(2→6)ラクトース含有化合物及びその使用               
    松岡 浩司; 照沼 大陽; 幡野 健; 鈴木 康夫, 特許権
    特許番号・登録番号:特許第5283033号
    J-Global ID:201303006772260047
  • チオグリコシド型シアル酸結合デンドリマー化合物               
    松岡 浩司; 照沼 大陽; 幡野 健; 鈴木 康夫, 特許権
    特許番号・登録番号:特許第5282258号
    J-Global ID:201303025187392021
  • ヒトノイラミニダーゼ阻害剤又はケミカルシャペロン組成物               
    松岡 浩司; 鈴木 香織; 伊藤 孝司, 特許権
    J-Global ID:201303048956795509
  • 糖修飾粒子およびその製造方法               
    照沼 大陽; 幡野 健; 松岡 浩司, 特許権
    特許番号・登録番号:特許第5205616号
    J-Global ID:201303060025007604
  • 蛍光性アミラーゼ基質及び該基質を用いたアミラーゼ活性測定方法               
    岡 博之; 松岡 浩司; 照沼 大陽; 幡野 健, 特許権
    特許番号・登録番号:特許第5167451号
    J-Global ID:201303087354208527
  • 立体保護を利用したオリゴ糖の合成方法               
    幡野 健; 高畑 徳允; 松岡 浩司, 特許権
    J-Global ID:201303067768569849
  • ウィルス、微生物類の検出方法               
    幡野 健; 松岡 浩司; 照沼 大陽, 特許権
    特許番号・登録番号:特許第5137081号
    J-Global ID:201303027515086572
  • シアル酸チオグリコシドポリマー               
    松岡 浩司; 照沼 大陽; 幡野 健; 鈴木 康夫, 特許権
    特許番号・登録番号:特許第5103613号
    J-Global ID:201303019802589949
  • ウィルス、微生物類及び毒素の検出方法               
    相澤 宏明; 幡野 健; 松岡 浩司, 特許権
    J-Global ID:201203039218609680
  • シアリルラクトサミン結合デンドリマー化合物               
    幡野 健; 照沼 大陽; 松岡 浩司; 森 知紀; 鈴木 康夫; 郭 潮潭, 特許権
    特許番号・登録番号:特許第4930929号
    J-Global ID:201303095477300412
  • 新規糖鎖担持カルボシランデンドリマーおよびその製造方法、並びにデング熱ウイルス感染阻害剤、抗ウイルス剤及び抗HIV剤のスクリーニング用標的物質               
    照沼 大陽; 幡野 健; 松岡 浩司; 鈴木 康夫; 左 一八, 特許権
    特許番号・登録番号:特許第4666941号
    J-Global ID:201103064702863718
  • 糖残基を有するオルガノポリシロキサンおよびその製造方法               
    吉武 誠; 照沼 大陽; 松岡 浩司; 幡野 健, 特許権
    特許番号・登録番号:特許第4043765号, 403765
    J-Global ID:201103077297712116
  • 糖残基を有するオルガノポリカルボシロキサンおよびその製造方法               
    吉武 誠; 照沼 大陽; 松岡 浩司; 幡野 健, 特許権
    特許番号・登録番号:特許第4043764号, 403764
    J-Global ID:201103033921296478
  • 糖修飾粒子およびその製造方法               
    照沼 大陽; 幡野 健; 松岡 浩司, 特許権
    J-Global ID:200903074095616347
  • 新規ラクトサミン誘導体とその製造方法               
    松岡 浩司; 照沼 大陽; 幡野 健, 特許権
    特許番号・登録番号:特許第3992510号, 3992510
    J-Global ID:201103068341484801
  • 新規糖鎖担持カルボシランデンドリマーおよびその製造方法、並びにデング熱ウイルス感染阻害剤、抗ウイルス剤及び抗HIV剤のスクリーニング用標的物質               
    照沼 大陽; 幡野 健; 松岡 浩司; 鈴木 康夫; 左 一八, 特許権
    J-Global ID:200903032551537409
  • ベロ毒素中和剤               
    松岡 浩司; 照沼 大陽; 幡野 健; 西川 喜代孝; 名取 泰博; 喜多 英二; 渡邊 美帆, 特許権
    J-Global ID:200903008869797550
  • 新規シアル酸供与体とその製造方法並びにそれを用いたシアル酸の導入方法               
    松岡 浩司; 照沼 大陽; 幡野 健; 坂入 信夫, 特許権
    J-Global ID:200903018368164218
  • ガラビオース結合カルボシランデンドリマー化合物               
    照沼 大陽; 松岡 浩司; 幡野 健; 名取 泰博; 西川 喜代孝, 特許権
    J-Global ID:200903027830436597
  • アミド結合型糖鎖含有カルボシランデンドリマーおよびその製造方法               
    松岡 浩司; 照沼 大陽; 幡野 健, 特許権
    J-Global ID:200903057419503662
  • 病原性微粒子吸着性中空糸及び病原性微粒子除去装置               
    畑中 研一; 松岡 浩司; 宮川 淳, 特許権
    J-Global ID:200903049683731603
  • 糖鎖含有カルボシランデンドリマー化合物とその製造方法並びにベロ毒素中和剤と抗ウイルス剤               
    松岡 浩司; 照沼 大陽; 葛原 弘美; 鈴木 康夫; 名取 泰博; 西川 喜代孝, 特許権
    J-Global ID:200903024133080980
  • ウィルス、微生物等の検出方法               
    特許権
  • シアリル a(2-6)ラクトース含有化合物及びその利用               
    特許権
  • シアリルラクトサミン担持デンドリマー化合物               
    特許権
  • 新規糖鎖担持カルボシランデンドリマーおよびその製造方法、並びにデング熱ウィルス感染阻害剤、抗ウィルス財及び抗HIV剤のスクリーニング用標的物質               
    特許権
  • 糖鎖含有カルボシランデンドリマー化合物とその製造方法並びにベロ毒素中和剤と抗ウィルス剤               
    特許権
  • SUGAR-MODIFIED PARTICLE AND METHOD FOR PRODUCTION THEREOF               
    特許権
  • Saccharide residue-functional organopolysiloxanes and method for the preparation thereof               
    特許権
  • Saccharide residue-functional organopolycarbosiloxanes and method for the preparation thereof               
    特許権
■ メディア報道
  • O157「毒素中和剤を開発」マウス服用で効果確認               
    本人以外, 産経新聞, 2004年2月8日付け, 朝刊30面, 2004年02月08日, [新聞・雑誌]
  • 「O157毒素に中和剤」のむだけで食中毒防止~マウスで実証~               
    本人以外, 東京新聞, 2004年2月8日付け, 朝刊26面, 2004年02月08日, [新聞・雑誌]
  • 大腸菌O157のベロ毒素「人工透析で血中から除去」糖鎖結合中空糸を利用               
    本人以外, 日刊工業新聞, 2003年2月3日付け, 朝刊5面, 2003年02月03日, [新聞・雑誌]
  • インフルエンザ~感染防ぐ新物質~ 埼玉大-静岡県立大 ウイルスに付着               
    本人以外, 日経産業新聞, 2002年12月18日付け, 朝刊13面, 2002年12月18日, [新聞・雑誌]
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