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Synthesis and Function of Modified Oligosaccharides

Research Project

Project/Area Number 06453212
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

HASHIMOTO Hironobu  Tokyo Institute of Technology, Faculty of Bioscience and Biotechnology Professor, 生命理工学部, 教授 (10016131)

Co-Investigator(Kenkyū-buntansha) YUASA Hideya  Tokyo Institute of Technology, Faculty of Bioscience and Biotechnology Assistant, 生命理工学部, 助手 (90261156)
Project Period (FY) 1994 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥7,200,000 (Direct Cost: ¥7,200,000)
Fiscal Year 1996: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 1995: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 1994: ¥4,500,000 (Direct Cost: ¥4,500,000)
Keywords5-Thioaldose / Fucosidase / Inhibitor / Fucosyltransferase / Sialyltransferase / Pseudooligosaccharide / Galactosyltransferase / Glycosyltransferase / CMP-シアル酸輸送タンパク / 修飾オリゴ糖 / グリコシダーゼ / グリコシルトランスフェラーゼ / アザ糖 / 阻害剤
Research Abstract

In order to elucidate the reaction machanisms of glucosidases and glycosyltransferases, various oligosaccharide mimics were synthesized and their biochemical behaviors were examined. Di-and trisaccharides having 5-thio-L-fucose residue at the non-reducing end were synthesized and the former analogs were proved to be effective as a linkage-specific inhibitor against alpha-L-fucosidase, while one (H type 2) of the latter analogs showed different behaviors from the natural trisaccharide toward the lectin and antibody. Further, synthetic routes of disaccharides having azasugar at the non-reducing end through amidine linkage were developed. Various glycosyl donor analogs of glycosyltransferases were synthesized. Among them, UDP-5-thio-GalNAc, GDP-5-thio-L-Fuc, and sialyl phosphonate analog of CMP-NeuNAc were found to be active as glycosyl donors, for beta-1,4-galactosyltransferase, alpha-L-fucosyltransferase, and alpha-sialytransferase, respectively.

Report

(4 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • 1994 Annual Research Report
  • Research Products

    (32 results)

All Other

All Publications (32 results)

  • [Publications] O.Tsuruta: "UDP-Ν-Acetyl-5-thio-galactosamine Is a Substrate of Lactose Synthase." Bioorg.Med.Chem.Lett.7. 2523-2526 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Izumi: "Synthesis of 5-Thio-L-fucose-Containing Disaccharides,as Sequence-Specific Inhibitors,and 2'Fucosyllactose,as a Substrate of α-L-Fucosidases." J.0rg.Chem.62. 992-998 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Hashimoto: "Synthesis of the First Tricomponent Bisubstrate Analogue That Exhibits Potent Inhibition against GlcNAc:β-1,4-Galactosyltransferase." J.Org.Chem.62. 1914-1915 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Yuasa: "Relative Nucleophilicity of the Two Sulfur Atoms in 1,5-Dithioglucopyranoside." Angew.Chem.Int.Ed.36. 868-870 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Izumi: "A Facile Synthesis of 5-Thio-L-fucose and 5-Thio-D-arabinose from D-Arabinose." Carbohydr.Res.280. 287-302 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Izumi: "Synthesis of 5-thio-L-fucose-containing blood group antigents H-type 2 and LewisX(Le^x)" Tetrahedron Lett.37. 1809-1812 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Suzuki: "Two Efficient Routes for Construction of Amidine-Linked Pseudosaccharide." Tetrahedron Lett.37. 5921-5924 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Osamu TSURUTA,Go SHINOHARA,Hideya YUASA,and Hironobu HASHIMOTO: "UDP-N-Acetyl-5-thio-galactosamine Is a Substrate of Lactose Synthase." Bioorg.Med.Chem.Lett.7. 2523-2526 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Masayuki IZUMI,Osamu TSURUTA,Satoru HARAYAMA,and Hironobu HASHIMOTO: "Synthesis of 5-Thio-L-fucose-Containing Disaccharides, as Sequence-Specific Inhibitors, and 2'-Fucosyllactose, as a Substrate of alpha-L-Fucosidases." J.Org.Chem.62. 992-998 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Hironobu HASHIMOTO,Tsuyoshi ENDO,and Yasuhiro KAJIYAMA: "Synthesis of the First Tricomponent Bisubstrate Analogue That Exhibits Potent Inhibition against GlcNAc : beta-1,4-Galactosyltransferase." J.Org.Chem.62. 1914-1915 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Hideya YUASA,Yujiro KAMATA,and Hironobu HASHIMOTO: "Relative Nucleophilicity of the Two Sulfur Atoms in 1,5-Dithioglucopyranoside." Angew.Chem.Int.Ed.36. 868-870 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Masayuki IZUMI,Osamu TSURUTA,and Hironobu HASHIMOTO: "A Facile Synthesis of 5-Thio-L-fucose and 5-Thio-D-arabinose from D-Arabinose." Carbohydr.Res.280. 287-302 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Masayuki IZUMI,Osamu TSURUTA,Hironobu HASHIMOTO,and Shin YAZAWA: "Synthesis of 5-Thio-L-fucose-contaning Blood Group Antigents H-type 2 and Lewis X(Lex)." Tetrahderon Lett.37. 1809-1812 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Katsuhiko SUZUKI,Takashi FUJII,Ken-ichi SATO,and Hironobu HASHIMOTO: "Two Efficient Routes for Construction of Amidine-Linked Pseudosaccharide." Tetrahedron Lett.37. 5921-5924 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Izumi: "A Facile synthesis of 5-thio-L-fucose and 5-thio-D-arabinose from D-arabinose" Carbohydr.Res.280. 287-302 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] H.Hashimoto: "Novel conversion of aldopyranosides into 5-thioaldopyranosides via an acyclic monothioacetal with inversion and retention of configuration at C-5" Carbohydr.Res.282. 207-221 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] K.Hiruma: "Efficient Synthesis of Pyruvic Acetals Carbohydrate Vicinal Diols:3,4,0-(1-Methoxycarbonyl)ethylidene-D-galactopyranoside and 5,6,0-(1-Methoxycarbonyl)ethylidene-D-galactofuranoside,via 1-Hydroxy-2-propanone Acetals." Carbohydr.Res.282. 299-306 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] H.Kakinuma: "Synthesis of 1',6'-Disubstituted Sucroses and their Behavior as Clucosyl Donors for a Microbial α-Glucosyltransferase." Carbohydr.Res.284. 61-72 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] M.Izumi: "Synthesis of 5-thio-L-fucose-containing blood group antigents H-type 2 and Lewis X (Le^x)" Tetrahedron Lett.37. 1809-1812 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] H.Hashimoto: "Synthesis of Methyl 5'-thio-α-Isomaltoside via an Acyclic Monothioacetal and Its Behavior toward Glucoamylase." Chem.Eur.J.2. 556-560 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] H.Yuasa: "Importance of Ring Sulfur and Anomeric Hydroxyl for Inhibitory Activity of 5-Thiofucose toward α-Fucosidases." Csrbohydr.Lett.2. 23-26 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Y. Kajihara: "Enzymic transfer of 6-modified D-galactosyl residues: synthsis of bianntenmary penta- and heptasaccharide having two 6-deoxy-D-galactose residues at the non -reducing end and evalation of 6-deoxy-D galactosyltransfer to glycoprotein using bovine β(1→4)-galactosyltransferase and UDP-6-deoxy-D-galactose" Carbohydr. Res.267. 273-294 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] K. Hiruma: "Structural elucidation of the component trisaccharide obtained form the acrosome reaction-inducing substance of the starfish Asterias ammureusis by chemical synthesis" J. Carbohydr. Chem.14. 879-883 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M. Izumi: "A Facile synthesis of 5-thio-L-fucose and 5-thio-D-arabinose from D-arabinose" Carbohydr. Res.280. 287-302 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] M. Izumi: "Synthesis of 5-thio-L-fucose-containing blood group antigents H-type 2 and Lewis X (Le^X)" Tetrahedron Lett.37. (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] H. Hashimoto: "Novel conversion of aldopyranosides into 5-thioaldopyranosides via an acyclic monothioacetal with inversion and retention of configuration at C-5" Carbohydr. Res.284. (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] H. Kakinuma: "Synthesis of 1', 6'-disubstituted sucroses and their behavior as donor substrates of the α-glucosyltransferase from Protaminabacter rubrum" Carbohydr. Res.285. (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] H. Hashimoto: "Synthesis of α-L-fucopyranosyl disaccharides with Thioglycosidic linkages and characterization of α-L-fucosidases from bovine kidney and epidiolymis by their inhibitory activities" Tetrahedron Asymmetry. 5. 2351-2366 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] H. Kakinuma: "Transglycosylation with 6'-chloro-6'-deoxy sucrose and immobilized isomaltulose-producing microorganisms using 2,2-dimethyl-1,3-dioxolane-4-methanol and its related compounds as acceptors. Steric and Chemical requirement of the glycosyl acceptor." Carbohydr. Res.264. 237-251 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 橋本弘信: "糖転移酵素の非天然型オリゴ糖阻害剤" 化学工業. 482-488 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Y. Kajihara: "Enzymic transfer of 6-modified D-galactosyl residues: synthsis of bianntenmary penta-and hepta-saccharide having two 6-deoxy-D-galactose residues at the non-reducing end and evalation of 6-deoxy-D-galactosyltransfer to glycoprotein using bovine β(1→4)-galactosyltransferase and UDP-6-deoxy-D-galactose" Carbohydr. Res.267. (1995)

    • Related Report
      1994 Annual Research Report
  • [Publications] K. Hiruma: "Structural elucidation of the component trisaccharide obtained form the acrosome reaction-inducing substance of the starfish Asterias ammureusis by chemical synthesis" J. Carbohydr. Chem.14. (1995)

    • Related Report
      1994 Annual Research Report

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Published: 1994-04-01   Modified: 2016-04-21  

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