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Synthesis of Branched Amino Polysaccharides

Research Project

Project/Area Number10650871
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 高分子合成
Research InstitutionSeikei University

Principal Investigator

KURITA Keisuke  Fac.of Engineering, Seikei University, Professor, 工学部, 教授 (30102180)

Co-Investigator(Kenkyū-buntansha) NISHIYAMA Yasuhiro  Fac.of Engineering, Seikei University, Assoc. Professor, 工学部, 助教授 (30286900)
Project Period (FY) 1998 – 1999
Project Status Completed(Fiscal Year 1999)
Budget Amount *help
¥1,500,000 (Direct Cost : ¥1,500,000)
Fiscal Year 1999 : ¥700,000 (Direct Cost : ¥700,000)
Fiscal Year 1998 : ¥800,000 (Direct Cost : ¥800,000)
KeywordsChitin / Chemical Modification / Branched Polysaccharide / Functional Polysaccharide Silylation / Glycosylation / Antimicrobial activity / Biodegradability / 生分解性 / 分枝型多糖 / キトサン / 分岐型多糖 / シリル化キチン / 反応前駆体 / 金属イオン吸着能
Research Abstract

Although chitin is an unutilized biomass resource, it is quite attractive as a specialty functional biopolymer owing to its distinctive biological activities as well as unique physicochemical properties, Our interest has been focused on the development of efficient chemical modifications of chitin so as to make possible construction of sophisticated molecular environments leading to the synthesis of polymeric materials with advanced functions.
A series of regioselective modification reactions of chitosan gave a derivative with a reactive group only at C-6, which was glycosylated with an oxazoline derived from glucosamine to introduce sugar branches. The degree of substitution was up to 0.6. The resulting branched chitin and chitosan were soluble in water and exhibited significant antimicrobial activity. They were degraded enzymatically, and the rate was dependent on the degree of substitution. Maltose also could be introduced using an orthoester of the disaccharide. Comb-shaped chitosan derivatives were prepared by reductive alkylation of aldehydes of poly (ethylene glycol); they were soluble and adsorbed metal cations.
In order to synthesize branched polysaccharides in a simple manner, trimethylsilylated chitin was prepared and evaluated as an organosoluble precursor for efficient modifications. Trimethylsilylation was more facile with β-chitin than α-chitin, and a fully silylated derivative was obtained. The silylated chitin was readily soluble in common organic solvents, and chitin films were easily prepared by casting and subsequent desilylation. It exhibited considerable reactivity in solution as confirmed by tritylation and glycosylation. The degrees of substitution for these reactions were 1.0 and 0.6, respectively, under appropriate conditions. Trimethylsilylated chitin has thus proved to be a superb precursor for modification reactions to allow synthesis of various derivatives from chitin.

Report

(3results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report

Research Products

(22results)

All Other

All Publications

  • [Publications] K. Kurita: "Comb-Shaped Chitosan Derivatives Having Oligo(ethylene glycol) Side Chains"Polym. Bull.. 42. 387-393 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Kurita: "Silylated Chitin: A New Precursor for Facile Modifications and Film Casting"Chem. Lett.. 771-772 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Kurita: "Enzymatic Degradation of β-Chitin: Susceptibility and the Influence of Deacetylation"Carbohydr. Polm. 42. 19-21 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Kurita: "Regioselectivity in Protection of Chitosan with the Phthaloyl Group"Chitin & Chitosan Res.. (in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Kurita: "Synthesis and Some Properties of Nonnatural Amino Polysaccharides: Branched Chitin and Chitosan"Macromolecules. (accepted).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Kurita: "Advances in Chitin Schience, Vol.3(2章分担執筆)"Rita Advertising. 517 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Kurita: "Advances in Chitin Schience, Vol.4(2章分担執筆)"European Chitin Society(in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Kurita, J, Amemiya, T. Mori, Y. Nishiyama: "Comb-Shaped Chitosan Derivatives Having Oligo (ethylene glycol) side chains"Polym. Bull.. 42. 387-393 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Kurita, M. Hirakawa, Y. Nishiyama: "Silylated Chitin: A New Precursor for Facile Modifications and Film Casting"Chem. Lett.. 771-772 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Kurita, Y. Kaji, M. Mori, Y. Nishiyama: "Enzymatic Degradation of β-Chitin: Susceptibility and the Influence of Deacetylation"Carbohydr. Polym.. 42. 19-21 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Kurita, M. Uno, Y. Saito, Y. Nishiyama: "Regioselectivity in Protection of Chitosan with the Phthaloyl Group"Chitin & Chitosan Res.. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Kurita, T. Kojima, Y. Nishiyama, M. Shimojoh: "Synthesis and Some Properties of Nonnatural Amino Polysaccharides: Branched Chitin and Chitosan"Macromolecules. (accepted).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Kurita: ""Efficient Chemical Modifications of Chitinous Materials for Developing Advanced Functions" and "Silylated Derivatives of Chitin as Organosoluble Precursors for Facile Modification Reactions""Advances in Chintin Science, Rita Advertising, Taipei, ROC. Vol.3. 8-15-141-146 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Kurita: ""Chemically Modified Chitionous Materials: Preparation and Properties" and "Graft Copolymerization of Methyl Methacrylate onto Mercapto-Chitin""Advances in Chintin Science, European Chitin Society. Vol.4(in press). (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K.Kurita: "Silylated Chitin:A New Precursor for Facile Modifications and Film Casting"Chem.Lett.. 771-772 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Kurita: "Comb-Shaped Chitosan Derivatives Having Oligo(ethylene glycol) Side Chains"Polym.Bull.. 42. 387-393 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Kurita: "Enzymatic Degradation of β-Chitin:Susceptibility and the Influence of Deacetylation"Carbohydr.Polym.. 42. 19-21 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Kurita: "Regioselectivity in Protection of Chitosan with the Phthaloyl Group"Chitin & Chitosan Res.. (in press).

    • Related Report
      1999 Annual Research Report
  • [Publications] K,Kurita: "Advances in Chitin Science,Vol 3(うち,2章執筆)"Rita Advertising. 517 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K,Kurita: "Advances in Chitin Science,Vol 4(うち,2章執筆)"European Chitin Society(in press).

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Kurita: "Comb-shaped chitosan derivatives having oligo (ethylene glycol) side chains" Polym.Bull.(in press).

    • Related Report
      1998 Annual Research Report
  • [Publications] K.Kurita: "Silylated chitin : A new organosoluble precursor for facile modifications and film casting" (発表予定).

    • Related Report
      1998 Annual Research Report

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Published : 1998-04-01   Modified : 2016-04-21  

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