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2002 Fiscal Year Final Research Report Summary

"CARBOHYDRATE MODULE METHOD" FOR A FACILE ASSEMBLY OF CELL SURFACE OLIGOSACCHARIDE MIMICS

Research Project

Project/Area Number 13555259
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field 高分子合成
Research InstitutionNagoya University

Principal Investigator

NISHIDA Yoshihiro  Nagoya University, DEPARTMENT OF MOLECULAR DESIGN & ENGINEERING, GRADUATE SCHOOL OF ENGINEERING, ASSOCIATE PROFESSOR, PhD, 工学研究科, 助教授 (80183896)

Co-Investigator(Kenkyū-buntansha) MATSUDA Kazuhiro  Nagoya University, DIVISON OF VIRUS, NATIONAL CANCER INSTITUTE, CHIEF RESEARCHER, PhD, ウイルス部, 主任研究官 (80251502)
KOBAYASHI Kazukiyo  Nagoya University, DEPARTMENT OF MOLECULAR DESIGN & ENGINEERING, GRADUATE SCHOOL OF ENGINEERING, PROFESSOR, PhD, 工学研究科, 教授 (10023483)
Project Period (FY) 2001 – 2002
Keywordsoligosaccharide / cell surface / mimic synthesis / carbohydrate module / polymerization / selectin / antagonist / sulfate
Research Abstract

A novel method to mimic the biologically active structure of cell surface oligosaccharide has been investigated in terns of carbohydrate module method. The method, thus established in this project, involves the segmentation of an oligosaccharide antigen into two simpler saccharides and the regeneration of the bioactive structure by their radical copolymerization with acrylamide. A series of carbohydrate modules constructing each of Lewis-X, sialyl Lewis-X, and 6-sulfo-sialyl Lewis-X antigens were mimicked by the module approach and evaluated for their potential as L-selectin antgonists, in which multivalent 6-sulfo-D-GlcNAc was found to possess high biological potential.

  • Research Products

    (27 results)

All Other

All Publications (27 results)

  • [Publications] Y.Nishida, H.Tamakoshi, K.Kobayashi, J.Thiem: "The First Bovine beta-1,4-Galactosyltransferase Reaction with an Acyclic Acceptor Substrate, 3-Acetamido-1,2-propanediol to Yield 3-O-beta-D-Galactopyranosyl-sn-glycerol Skeleton"Organic Letters. 3. 1-3 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yoshihiro Nishida, Masaya Suzuki, Kazukiyo Kobayashi, Yoshiharu Toriumi, Hideki Hashimoto: "Crystal Structure of Methyl 5-Acetamido-2-tert-butyl-2-methyl-1,3-benzodioxole-4-carboxylate"Analytical Science. 17. 685-686 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Kato, A.Yashiro, A.Mizuno, Y Nishida, K.Kabayashi, H.Shinohara: "Syntheses and Biological Evaluations of alpha-D-Mannosyl [60] Fullerenols"Biorog.Med.Chem.Lett.. 11. 2935-2937 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Dohi, Y.Nishida, H.Tanaka, K.Kobayashi: "Methylsalicyl beta-D-Galactopyranoside, A Non-Malodorous ThiO Glycosylation Donor For the Synthesis of Globosyl alpha-(1-4)-Linkages"Syn Lett.. 1446-1448 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Sasaki, Y.Nishida, T.Tsurumi, H.Uzawa, H.Kondo, K.Kobayashi: "Facile Assembly of cell surface oligosaccharide mimics by copolymerization of carbohydrate modules"Angew.Chem.Int.Ed.,. 41. 4463-4467 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Dohi, Y.Nishida (他6名): "Molecular Design and Biological Potential of Galacto-type Trehalose as a Non-natural Ligand of Shiga Toxins"Organic Letters. 4. 355-357 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Dohi, Y.Nishida, T.Takeda, K.Kobayashi: "Convenient use of Non-malodorous Thio Glycosylation Donors for the Synthesis of multivalent Globo-and iso-globosyl trisaccharides"Carbohydrate Research. 337. 983-989 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Tanaka, Y.Nishida, Y.Furuta, K.Kobayashi: "A convenient synthetic pathway for multivalent assembly of aminoglycoside antibiotics staffing from Amikacin"Bioorganic Medicinal Chemistry Letter. 12. 1723-1726 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Uzawa, S.Kamiya, H.Dohi, Y.Nishida (他5名): "A Quartz Crystal Microbalance Method for Rapid Detection and Differentiation of Shiga Toxins by Applying a Monoalkyl Globobioside as the Toxin Ligand"Biomacromolecules. 3. 411-414 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Shingu, Y.Nishida, H.Dohi, K.Matsuda, K.Kobayashi: "Convenient access to halide ion-catalyzed a-glycosylation free from noxious fumes at the donor synthesis"Journal of Carbohydrate Chemistry. 21. 605-611 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Miura, Y.Sasao, H.Dohi, Y Nishida, K.Kobavashi: "Self-assembled monolayers of globotriaosylceramide (GB3) mimics: surface-sepcific affinity with Shiga toxins"Analytical Biochemistry. 310. 27-35 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Uzawa, Y.Nishida, K.Sasaki, N.Minoura, K.Kobayashi: "Synthetic Potential of Molluscan Sulfatases for the Library Synthesis of Regioselectively O-Sulfonated D-Galacto-Sugars"Chem.Bio.Chem,. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Shingu, Y.Nishida, H.Dohi, K.Kobayashi: "An easy access to Halide ion-catalytic alpha-glycosylation using carbon tetrabromide and triphenylphosphine as multifunctional agents"Org.Biomol.Chem.,. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y Nishida, Y Shingu, H Dhoi, K Kobayashi: "One-pot alpha-glycosylation method using Appel Agents in N,N-Dimethylformamide"Organic Letters. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Nishida, H.Tamakoshi, K.Kobayashi, J.Thiem: "The First Bovine beta-l, 4-Galactosyltransferase Reaction with an Acyclic Acceptor Substrate, 3-Acetamido-l, 2-propanediol to Yield 3-O-beta-D-Galactopyranosyl-sn-glycerol Skeleton"Org Lett.. 3. 1-3 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yoshihiro Nishida, Masaya Suzuki and Kazukiyo Kobayashi, Yoshiharu Toriumi and Hideki Hashimoto: "Crystal Structure of Methyl 5-Acetamido-2-tert-butyl-2-methy1-1, 3-benzodioxole-4-carboxylate"Anal.Sci.. 17. 685-686 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Haruhito Kato, Arihiro Yashiro, Akiko Mizuno, Yoshihiro Nishida, Kazukiyo Kabayashi, and Hisanori Shinohara: "Syntheses and Biological Evaluations of alpha-D-Mannosyl [60] Fullerenols"Biorog.Med.Chem.Lett.. 11. 2935-2937 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hirofumi Dohi, Yoshihiro Nishida, Hidehiko Tanaka, and Kazukiyo Kobayashi: "Methylsalicyl beta-D-Galactopyranoside, A Non-Malodorous Thio Glycosylation Donor For the Synthesis of Globosyl alpha-(l-4)-Linkages"Synlett. 1446-1448 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hirofumi Dohi, Yoshihiro Nishida, Yuki Furuta, Hirotaka Uzawa, Shin-ichiro Yokoyama, Saori Ito, Hiroshi Mori, Kazukiyo Kobayashi: "Molecular Design and Biological Potential of Galacto-type Trehalose as a Non-natural Ligand of Shiga Toxins"Org.Lett.. 4. 355-357 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Uzawa, S.Kamiya, H.Dohi, Y.Nishida, N.Minoura, K.Taguchi, S.-I.Yokoyama, H.Mori and K.Kobayashi: "A Quartz Crystal Microbalance Method for Rapid Detection and Differentiation of Shiga Toxins by Applying a Monoalkyl Globobioside as the Toxin Ligand"Biomacromolecules. 3. 411-414 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Tanaka, Y.Nishida, Y.Furuta, K.Kobayashi: "A convenient synthetic pathway for multivalent assembly of aminoglycoside antibiotics starting from Amikacin"Bioorg.Med.Chem.Lett.. 12. 1723-1726 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Miura, Y.Sasao, H.Dohi, Y.Nishida, K.Kobayashi: "Self-assembled monolayers of globotriaosylceramide (Gb3) mimics : surface-specific affinity with Shiga toxins"Anal.Biochem.. 310. 27-35 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Shingu, Y.Nishida, H.Dohi, K.Matsuda, K.Kobayashi: "Convenient access to halide ion-catalysed alpha-glycosylation free from noxious fumes at the donor synthesis"J.Carbohydr.Chem.. 21. 605-611 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Sasaki, Y.Nishida, T.Tsurumi, H.Uzawa, H.Kondo, K.Kobayashi: "Facile Assembly of cell surface oligosaccharide mimics by copolymerization of carbohydrate modules"Angew.Chem.Int.Ed.. 41. 4463-4467 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hirotaka Uzawa, Yoshihiro Nishida, Kenji Sasaki, Norihiko Minoura, and Kazukiyo Kobayashi: "Synthetic Potential of Molluscan Sulfatases for the Library Synthesis of Regioselectively O-Sulfonated D-Galacto-Sugars"Chem.Bio.Chem.. in press. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Shingu, Y.Nishida, H.Dohi, K.Kobayashi: "An easy access to Halide ion-catalytic alpha-glycosylation using carbon tetrabromide and triphenylphosphine as multifunctional agents"Org.Biomol.Chem.. in press. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Nishida, Y.Shingu, H.Dohi, K.Kobayashi: "Onepot alpha-glycosylation method using Appel Agent in N, N-Dimethylformamide"Org.Lett.. in press. (2003)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2004-04-14  

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