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Chemical synthesis of animal cell-surface glycoconjugates and analysis of the biological functions

Research Project

Project/Area Number 03660132
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionGifu University

Principal Investigator

HASEGAWA Akira  Gifu University, Professor Applied Bioorganic Chemistry,, 農学部, 教授 (10026429)

Co-Investigator(Kenkyū-buntansha) KISO Makoto  Gifu University, Professor Applied Bioorganic Chemistry,, 農学部, 教授 (90092931)
Project Period (FY) 1991 – 1992
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1992: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1991: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsGangliosides / Sialoglycolipids / Sialo-oligosaccharides / Oligosaccharide Recognized by Selectins / N-Acetylneuraminic Acid / Sialic Acid / alpha-Glycoside of Sialic Acids / Ceramide / シアル酸のα-グリコシド / セラミド / 細胞接着因子 / シアル酸含百糖脂質 / シアリルールイスX / ガン転位機作 / 感染症 / ラクト系列ガングリオシド
Research Abstract

The facile regio- and stereocontrolled alpha-glycosylation of sialic acids with several sugar residues are now well studied and high yields of desired products are possible either by DMTST or NIS/TfOH in acetonitrile under kinetically controlled conditions. By using this procedure, a variety of gangliosides, such as GM4, GM3, GM2, GM1, GM1b, GD1a, lacto and neolacto-tetraosyl ceramides, sialyl Le^x, and their positional isomers, have systematically been synthesized. Sialyl Le^x and its related compounds are very attractive molecules related to cancer methastasis, inflammation and other biological activities. We have also synthesized various analogs of gangliosides, containing thioglycosidic linkages, modified sialic acids, and pseudo-ceramides. Some of the thioglycosides analogs showed potential inhibition of the influenza A viruses. We hope that the evaluation of these compounds along with the native gangliosides for their biological properties will not only elucidate unknown aspects of structural relations of native gangliosides but also contribute to the development of novel medicinal therapeutic strategies.

Report

(3 results)
  • 1992 Annual Research Report   Final Research Report Summary
  • 1991 Annual Research Report
  • Research Products

    (30 results)

All Other

All Publications (30 results)

  • [Publications] Akira Hasegawa: "Synthesis of the methyl thioglycosides of deoxy-N-ace-tyl-neuraminic acids for use as glycosyl donors" Carbohydrate Research. 230. 257-272 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Akira Hasegawa: "Synthesis of a series of gangliosides GM_3 analogs cont-aining a deoxy-N-acetylbeuraminic acid residue" Carbohydrate Research. 230. 273-288 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Carrol Foxall: "The three members of the selectin receptor family recognize a common carbohydrate epitope,the sialyl lewis X oligosaccharide" The Journal of Cell Biology. 117. 895-902 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Franz-Georg Hanisch: "Sialyl lewis^x antigen as defined by monoclonal antibody AM-3 is a marker of dysplasia in the colnic adenoma-carcinoma sequence" Cancer Research. 52. 3138-3144 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Margot Larkin: "Spectrum of sialylated and nonsislylated fuco-oligo-saccharides bound by the endothelial-leukocyte adhesion molecule E-selectin" The Journal of Biological Chemistry. 267. 13661-13668 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Akira Hasegawa: "Stereocontrolled synthesis of sialyl lewis X epitope and its ceramide derivatives" Journal of Carbohydrate Chemistry. 11. 645-658 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Akira Hasegawa: "Carbohydrates-Synthetic Methods and Applications in Medicinal Chemistry" Kodanscha-VCH, 406 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 長谷川 明: "糖鎖工学" 産業調査会, 680 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Akira Hasegawa: "Synthesis of the methyl thioglycosides of deoxy-N-acetylneuraminic acids for use as glycosyl donors" Carbohydr. Res.230. 257-272 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Akira Hasegawa: "Synthesis of a series of gangliosides GM3 analogs containing a deoxy-N-acetylneuraminic acid residures" Carbohydr. Res.230. 273-288 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Carrol Foxall: "The three members of the selectin receptor family recognize a common carbohydrate epitope, the sialyl lewis^x oligosaccharide" The Journal of Cell Biology. 117. 895-902 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] F-Georg Hanisch: "Sialyl lewis^x antigen as defined by monoclonal antibody AM-3 ia a marker of dysplasia in the colonic adenoma-carcinoma sequence" Cancer Research. 52. 3138-3144 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Margot Larkin: "Spectrum of sialylated and non-sialylated fuco-oligosaccharides bound by the endothelial-leucocyte adhesion molecule E-selectin" The Journal of Biol. Chemistry. 267. 13661-13668 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Akira Hasegawa: "Stereocontrolled synthesis of sialyl lewis X epitope and its ceramide" Journal of Carbohydrate Chemistry. 11. 645-658 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Akira Hasegawa: Kodanscha-VCH. Carbohydrates-Synthetic Methods and Applications in Medicinal Chemistry, 406 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Akira Hasegawa: Sangyo-Chosakai. Sugar-Chain Technology, 680 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Akira Hasegawa: "Synthesis of the methyl thioglycosides of deoxy-N-ace-tyl-neuraminic acids for use as glycosyl donors" Carbohydrate Research. 230. 257-272 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Akira Hasegawa: "Synthesis of a series of ganglioside GM3 analogs containing a deoxy-N-acetylneuraminic acid residue" Carbohydrate Research. 230. 273-288 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Carrol Foxall: "The three members of the selectin receptor family recognize a common carbohydrate epitope,the sialyl lewis^x oligosaccharide" The Journal of Cell Biology. 117. 895-902 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Franz-Georg Hanisch: "Sialy lewis^x antigen as defined by monoclonal antibody AM-3 is a marker of dysplasia in the colonic adenomacarcinoma sequence" Cancer Research. 52. 3138-3144 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Margot Larkin: "Spectrum of Sialylated and nonsialylated fuco-oligo-saccharides boun by the endothelial-leukocyte adhesion molecule E-selectin" The Journal of Biological Chemistry. 267. 13661-13668 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Akira Hasegawa: "Stereocontrolled synthesis of Sialyl lewis X epitope and its ceramide derivatives" Journal of Carbohydrate Chemistry. 11. 645-658 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Akira Hasegawa: "Carbohydrates-Synthetic Methods and Applications in Medicinal Chemistry" Kodansha-VCH, 406 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] 長谷川 明: "糖鎖工学" 産業調査会, 680 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Akira Hasegawa: "A facile,largeーscale preparation of the methylー2ーthioglycoside of Nーacetylneuraminic acid,and its usefulness for the αーstereoselective syntnesis of sialoglycosides" Carbohydrate Research. 212. 277-281 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Akira Hasegawa: "Synthesis of cerebroside,lactosyl ceramide,and ganglioside GM_3 analogs containing βーthioglycosidically linked ceramide" Carbohydrate Research. 214. 43-53 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Akihiko Kameyama: "Total synthesis of tumorーassociated ganglioside,sialyl Lewis X" Journal of Carbohydrate Chemistry. 10. 549-560 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Akira Hasegawa: "Total synthesis of sialylーα(2ー6)ーlactotetraosyl ceramide and sialylーα(2ー6)ーneolactotetraosy cermide" Journal of Carbohydrate Chemistry. 10. 439-459 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] David Tyrrell: "Structural requirement for the carbohydrate ligand of Eーselectin" Procceding National Academy of Science USA. 88. 10372-10376 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Akio Takada: "Adhesion of human cancer cells to vascular endothelium mediated by a carbohydrate antigen,sialyl Lewis X" Biochemical and Biophysical Research Communication. 179. 713-719 (1991)

    • Related Report
      1991 Annual Research Report

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Published: 1991-04-01   Modified: 2016-04-21  

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