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Synthesis of functional Amino Polysaccharides by Branching of Linear Polysaccharides

Research Project

Project/Area Number 12650872
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  Seikei University, Dept.Of Applied Chemistry, Professor, 工学部, 教授 (30102180)

Co-Investigator(Kenkyū-buntansha) SHIMOJOH Manabu  Toyo Suisan Kaisha, Div, of research, Researcher, 研究員
HARATA Manabu  Seikei University, Dept.Of Applied Chemistry, Reserch Associate, 工学部, 嘱託助手
Project Period (FY) 2000 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 2001: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2000: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsChitin / Chemical modification / Branched polysaccharide / Functional Polysaccharide / Phthaloylation / Silylation / Glycosylation / Antimicrobial activity / 抗菌性 / セルロース
Research Abstract

Chitin is important as an unutilized biomass resource in view of its high potential in various fields. Our interest has been focused on the synthesis of chitin derivatives with advanced functions, particularly those having branches, because of the distinctive biological activities as well as unique physicochemical properties of this amino polysaccharide.
Although chemical modifications of chitin are generally difficult, a series of regioselective and quantitative modification reactions became possible using N-phthaloyl-chitosan. Based on this precursor, branched chitin and chitosan were prepared. The resulting products were water-soluble and exhibited various interesting properties such as biodegradability and antimicrobial activity. Phthaloylated chitosan has thus proved to be an indispensable precursor for efficient modifications, but phthaloylation usually results in partial O-phthaloylation besides N-phthaloylation. In dimethylformamide containing some water, however, chemoselectively N-phthaloylated chitosan could be prepared in one-step.
Trimethylsilylation of chitin was also examined in detail to give a fully substituted product. It was readily soluble in common solvents and showed high reactivity in some reactions. For instance, glycosylation of silylated chitin gave branched chitin, and this process is much simpler than that based on N-phthaloyl-chitosan.
Mercapto-chitin easily generated free radicals on mild heating due to the presence of labile mercapto groups. Graft copolymerization of methyl methacrylate thus proceeded efficiently to give chitin-graft-poly(methyl methacrylate). The methyl methacrylate units in the introduced side chains could be hydrolyzed under appropriate conditions to form sodium methacrylate units, which were in turn transformed into methacrylic acid units by treatment with acid. These modifications of the side chains enabled fine control of properties including solubility, hygroscopicity, and biodegradability.

Report

(3 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • Research Products

    (23 results)

All Other

All Publications (23 results)

  • [Publications] K.Kurita: "Controlled Functionalization of the Polysaccharide Chitin"Prog. Polyrn. Sci.. 26. 1921-1971 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Kurita: "Chemoselective Protection of the Amino Groups of Chitosan by Controlled Phthalovlation : Facile Preparation of a Precursor Useful for Chemical Modifications"Biomacromolecules. 3. 1-4 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Kurita: "Graft Copolymerization of Methyl Methacrylate onto Mercaptochitin and Some Properties of the Resulting Hybrid Materials"Biomacromolecules. 3. 147-152 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Kurita: "Polymeric Asymmetric Reducing Agents : Preparation and Reducing Performance of Chitosan/Dihydronicotinamide Conjuqates Having L-and D-Phenylalanine Spacer Arms"Carbohydr. Polym.. 47. 7-14 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Kurita: "N-Alkylation of Chitin and Some Characteristics of the Novel Derivatives"Polym. Bull.. (in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Kurita: "Synthesis and Asymmetric Reducing Performance of Chitin/Dihydronicotinamide Conjugates Having Glycine or L-Leucine Spacer Arms"Biomacromolecules. (in press).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Kurita: "Chitin and Chitosan-Chitin and Chitosan in Life Science(編集および分担執筆)"Kodansha Scientific. 340-347,366-367,368-369 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Kurita: "Advances in Chitin Science(分担執筆)"European Chitin Society(in press). (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Kurita,: "Controlled Functionalization the of Polysaccharide Chitin"Prog. Polym. Sci. 26. 1921-1971 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Kurita, H. Ikeda, Y. Yoshida, M. Shimojoh, and M. Harata: "Chemoselective Protection of the Amino Groups of Chitosan by Controlled Phthaloylation : Facile Preparation of aPrecursor Useful for Chemical Modifications"Biomacromelecules. 3. 1-4 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Kurita, M. Inoue, and M. Harata,: "Graft Copolymerization of Methyl Methacrylate onto Mercaptochitin and Some Properties of the Resulting Hybrid Materials"Biomacromelecules. 3. 147-152 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Kurita, M. Hayakawa, Y. Nishiyama, and M. Harata,: "Polymeric Asymmetric Reducing Agents : Preparation and Reducing Perfomance of Chitosan/Dihydronicotinamide Conjugates Habing L-and D-Phenylalanine Spacer Arms"Carbohydr. Polym. 47. 7-14 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Kurita, S. Mori, Y. Nishiyama, and M. Harata: "N-Alkylation of Chitin and Some Characteristics of the Novel Derivatives"Polym. Bull.. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K. Kurita, T. Nishibori, and M. Harata: "Synthesis and Asymmetric Reducing Perfomance of Chitin/Dihydronicotinamide Conjugates Having Glycine or L-Leucine Spacer Arms"Biomacromolecules. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] K.Kurita: "Controlled Functionalization of the Polysaccharide Chitun"Prog. Polym. Sci.. 26. 1921-1971 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Kurita: "Polymeric Asymmetric Reducing Agents: Preparation and Reducing Performance of Chitosan/Dihydronicotinamide Conjugates Haying L-and D-Phenylalanine Spacer Arms"Carbohydr. Polym.. 47. 7-14 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Kurita: "Chemoselective Protection of the Amino Groups of Chitosan by Controlled: Phthaloylation: Facile Preparation of a Precursor Useful for Chemical Modifications"Biomacromolecules. 3. 1-4 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Kurita: "Graft Copolymerization of Methyl Methacrylate onto Mercaptochitin and Some Properties of the Resulting Hybrid Materials"Biomacromolecules. 3. 147-152 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Kurita: "N-Alkylation of Chitin and Some Properties of the Novel Derivatives"Polym. Bull.. (in press). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Kurita: "Trimethylsilylated Chitins: Synthesis, Properties, and Modification Reactions (分担執筆)"European Chitin Society (in press). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Kurita: "Chitin and Chitosan -Chitin and Chitosan in Life Science (分担執筆)"Kodansha Scientific. 340-347, 366-367, 368-369 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] K.Kurita: "Controlled Functionalization of the Polysaccharide Chitin"Prog.Polym.Sci.. (in press).

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Kurita: "Polymeric Asymmetric Reducing Agents : Preparation and Reducing Performance of Chitosan/NADH conjugates....."Carbohydr.Polym.. (in press).

    • Related Report
      2000 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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