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Synthesis of Branched Polysaccharides Having Hypoglycaemic Activity

Research Project

Project/Area Number 07651074
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 高分子合成
Research InstitutionTokyo Institute of Technology

Principal Investigator

HATANAKA Kenichi  Tokyo Institute of Technology, Department of Biomolecular Engineering, Associate Professor, 生命理工学部, 助教授 (70167584)

Project Period (FY) 1995 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1997: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1996: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1995: ¥800,000 (Direct Cost: ¥800,000)
KeywordsChemo-Enzymatic Synthesis / Branched Polysaccharide / Hypoglycaemic Activity / D-Xylose / Imidate Method / Curdlan / Natural Polysaccharide / Ring-Opening Polymerization / 分岐多糖 / 血統降下作用 / 合成多糖 / 無水糖 / グルコピラナン / 酵素反応 / α-D-グルコース
Research Abstract

2,4-Di-O-benzyl- (1*6) -alpha-D-glucopyranan which was prepared by cationic ring-opening polymerization of an anhydro glucose derivative was xylosylated at the C-3 position to give xylopyranosyl glucopyranan derivatives. Stereoselectivity of the xylosylation with xylopyranosyl trichloroacetimidate as glycosylating reagent was low. Glucosyl branches were introduced into curdlan ((1*3)-beta-D-glucopyranan) for the purpose of improvement of physical properties of natural polysaccharides. Curdlan was protected by regioselective tritylation at C-6 position, followed by phenylcarbamoylation at C-2 and C-4. Selectively deprotected (detritylated) curdlan was glucosylated to give (1*3) -beta-D-glucopyranan derivative with glucopyranosyl branches. Deprotections of the obtained branched polysaccharide were also attempted. Natural polysaccharide curdlan was then dimethoxytritylated, phenylcarbamoylated, and dedimethoxytritylated in order to prepare a regioselectively protected polysaccharide. The regioselectively protected curdlan was subsequently glucosylated with glucopyranosyl trichloroacetimidate.

Report

(4 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • 1995 Annual Research Report
  • Research Products

    (50 results)

All Other

All Publications (50 results)

  • [Publications] K.-I.Kanno, Y.Kobayashi, S.-I.Nishimura, H.Kuzuhara, and K.Hatanaka: "Synthesis of (1→6)-β-Linked N-Acetyl-D-glucosamine Oligosaccharide" Journal of Carbohydrate Chemistry. 14. 481-490 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.Hatanaka, T.Minamisawa, and K.-I.Kanno: "Syntheses of Polysaccharides Having Various Contents of Carboxyl Groups by Ring-Opening Copolymerization." Polymer Journal. 27. 1016-1020 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] 畑中 研一、冨岡 伸之、太田 早苗、門倉 健、粕谷 マリア: "天然多糖の修飾による分枝多糖の化学合成" 日本接着学会誌. 32. 256-260 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.-I.Kanno, T.Minamisawa, and K.Hatanaka: "Synthesis of Glycosaminoglycan-Like Copolysaccharide Derivatives" Polymer Journal. 29. 773-774 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] 畑中 研一、太田 早苗、門倉 健、粕谷 マリア: "分枝多糖誘導体の精密合成" 高分子論文集. 54. 947-950 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] N.Ota and K.Hatanaka: "Clarification of the Transfer Reaction in the Synthesis of Manno-Oligosaccharide" Macromolecules. 31(印刷中). (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.Hatanaka et al.: "Polysaccharides in Medicinal Applications" Edited by S.Dumitriu,MARCEL DEKKER,INC., 794 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] 畑中 研一、西村 紳一郎、大内 辰郎、小林 一清: "糖質の科学と工学" 講談社サイエンティフィク, 166 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.-I.Kanno, Y.Kobayashi, and K.Hatanaka: "Effects of Electron-Withdrawing Groups at C-2 Position of 1,6-Anhydro-Sugars on Their Polymerizabilities" Polym.J.27. 71-77 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Kunou, T.Ohtsuki, T.Akaike, and K.Hatanaka: "Mollification of Cytotoxicity of Sulfated Polysaccharides by Fibroblast Growth Factors" J.Carbohydr.Chem.14. 659-665 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.-I.Kanno, Y.Kobayashi, S.-I.Nishimura, H.Kuzuhara, and K.Hatanaka: "Synthesis of (1*6) -beta-Linked N-Acetyl-D-glucosamine Oligosaccharide" J.Carbohydr.Chem.14. 481-490 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.-I.Kanno, W.Kinoshita, K.Kobayashi, and K.Hatanaka: "Synthesis of Stereoregular Polysaccharide Derivatives Carrying cis-Oriented 2,3-Di-O-Alkyl Chains" Polym.J.27. 911-916 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.Hatanaka, T.Minamisawa, and K.-I.Kanno: "Syntheses of Polysaccharides Having Various Contents of Carboxyl Groups by Ring-Opening Copolymerization" Polym.J.27. 1016-1020 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Kunou and K.Hatanaka: "Effects of Sulfated Polysaccharide and Acidic Fibroblast Growth Factor on 3T3-L1 Fibroblasts" Carbohydr.Polym.28. 107-112 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.Hatanaka, N.Tomioka, S.Ohta, T.Kadokura, and M.C.Kasuya: "Chemical Synthesis of Branched Polysaccharide by Glycosylation of Natural Polysaccharide" Nippon Secchakugakkaishi. 32. 256-260 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.Hatanaka, H.Takeshige, K.-I.Kanno, A.Maruyama, J.Oishi, Y.Kajihara, and H.Hashimoto: "New Polymeric Inhibitor of Galactosyl Transferase" J.Carbohydr.Chem.16. 667-672 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.-I.Kanno, T.Minamisawa, and K.Hatanaka: "Synthesis of Glycosaminoglycan-Like Copolysaccharide Derivatives" Polym.J.29. 773-774 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] N.Ota, K.Hirano, M.Warashina, A.Andrus, B.Mulah, K.Hatanaka, and K.Taira: "Structural Analysis of Nucleic Acids by Using Fluorescence Resonance Energy Transfer (FRET)" Nucelic Acids Symposium Series. 37. 207-208 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.Hatanaka, S.Ohta, T.Kadokura, and M.C.Kasuya: "Synthesis of Branched Polysaccharide Derivatives." Kobunnshi Ronbunshu. 54, [12]. 947-950 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] M.Kunou and K.Hatanaka: "The Effect of Growth Factors on the Cytotoxicity of Sulfated Polysaccharides" Carbohycr.Polym.(in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] A.Kai, H.Karasawa, M.Kikawa, K.Hatanaka, K.Matsuzaki, T.Mimura, and Y.Kaneko: "Biosynthesis of ^<13>C-Labeled Branched Polysaccharides by Pestalotiopsis from ^<13>C-Labeled Glucose and the Mechanism of Formation" Carbohycr.Polym.(in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] N.Ota, K.Hirano, M.Warashina, A.Andrus, B.Mullah, K.Hatanaka, and K.Taira: "Determination of interactions between structured nucleic acids by fluorescence resonance energy transfer (FRET) : selection of target sites for functional nucleic acids" Nucleic Acids Res.(in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] N.Ota and K.Hatanaka: "Clarification of the Transfer Reaction in the Synthesis of Manno-Oligosaccharide" Macromolecules. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Edited by R.A.Pethrick: Polymer Yearbook 12. harwood academic publishers, 261-268 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Edited by S.Dumitriu: Polysaccharides in Medicine and Biotechnology. MARCEL DEKKER,INC, 3-20 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Edited by J.C.Salamone: The Polymeric Materials Encyclopedia : Synthesis, Properties, and Applications. CRC Press, Inc., 2954-2959,6713-6717 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Edited by R.A.Pethrick: Polymer Yearbook 13. harwood academic publishers, 293-297 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Edited by R.A.Pethrick: Polymer Yearbook 14. harwood academic publishers, 207-212 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] K.Hatanaka, H.Takeshige, K.-I.Kanno, A.Maruyama, J.Oishi, Y.Kajihara, and H.Hashimoto: "New Polymeric Inhibitor of Galactlosy Transferase" Journal of Carbohydrate Chemistry. 16・4 & 5. 667-672 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] K.-I.Kanno, T.Minamisawa, and K.Hatanaka: "Synthesis of Glycosaminoglycan-like Copolysaccharide Derivative" Polymer Journal. 29・9. 773-774 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] N.Ota, K.Hirano, M.Warashina, A.Andrus, B.Mulah, K.Hatanaka, and K.Taira: "Structural Analysis of Nuclcic Acids by Using Fluorescence Resonance Energy Transfer(FRET)" Nucelic Acids Symposium Series. 37. 207-208 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 畑中研一、太田早苗、門倉健、粕谷マリア: "分枝多糖誘導体の精密合成" 高分子論文集. 54・12. 947-950 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] M.Kunou and K.Hatanaka: "The effect of Growth Factors on the Cytotoxicity of Sulphated Polysaccharides" Carbohydrate Polymers. (印刷中). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] A.Kai, H.Karasawa, M.Kikawa, K.Hatanaka, K.Matsuzaki, T.Mimura, and Y.Kaneko: "Biosynthesis of ^3C-Labeled Polysaccharides by Pestalotiopsis from ^3C-Labeled Glucose and the Mechanism of Formation" Carbohydrate Polymers. (印刷中). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] 畑中研一、西村紳一郎、大内辰郎、小林一清: "糖質の科学と工学" 講談社サイエンティフィク, 166 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] V.V.Myasoedova et.al: "Polymer Yearbook 14" harwood academic publishers, 293 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 畑中研一、富岡伸之ら: "天然多糖の修飾による分枝多糖の化学合成" 日本接着学会誌. 37. 256-260 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 南澤俊和、畑中研一: "生理活性を有する酸性多糖" 繊維学会誌. 52. P63-P68 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 畑中研一: "生理活性の高い硫酸化多糖を求めて" 化学. 52. 68-69 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] K.Hatanaka et al.: "New Polymeric Inhibitor of Galactosyl Transferase" Journal of Carbohydrate Chemistry. 16(印刷中). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] K.Hatanaka et al.: "Synthesis and Biological Functions of Uridine-Containing Polystyrene" Proceedings of XVIII International Carbohydrate Symposium. 18. 573 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 畑中研一、西村紳一郎、大内辰郎、小林一清: "糖質の科学と工学" 講談社サイエンティフィク, 176 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] K.Hatanaka et al.: "Polysaccharides in Medicinal Applications" Marcel Dekker,Inc,(New York), 794 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 南澤俊和: "生理活性を有する酸性多糖" 繊維学会誌. 52. P63-P68 (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Kenichi Hatanaka: "Syntheses of Polysaccharides Having Various Contents of Carboxyl Groups by Ring-Opening Copolymerization" Polymer Journal. 27. 1016-1020 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Ken-Ichi Hanno: "Synthesis of Stereoregular Polysaccharide Carrying 2,3-Di-O-alkyl Chains" Polymer Journal. 27. 911-916 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Kenichi Hatanaka: "A New Synthetic Inhibitor of Glycosyl Transferase" Glycoconjugate Journal. 12. 458-458 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Ken-Ichi Kanno: "Synthesis of(1→6)-β-Linked N-Acetyl-D-glucesamine Oligosaccharide" Journal of Carbohydrate Chemistry. 14. 481-490 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Megumi Kunou: "Mollification of Cytotoxicity of Sufated Polysaccharides by Fibroblast Growth Factors" Journal of Carbohydrate Chemistry. 14. 659-665 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] A.L.Rusanov: "Polymer Yearbook 12" harwood academic publishers, 336 (1995)

    • Related Report
      1995 Annual Research Report

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Published: 1995-04-01   Modified: 2016-04-21  

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