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Synthesis of Cell-Recognizable Sugar-Peptide Conjugates by Living Ring-Opening Polymerization

Research Project

Project/Area Number 07651081
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

OKADA Masahiko  School of Agricultural Sciences, Nagoya University Professor, 農学部, 教授 (20023103)

Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1996: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1995: ¥1,500,000 (Direct Cost: ¥1,500,000)
KeywordsGlycopeptide / Living Polyemrization / Ring-Opening Polymerization / Block Copolymer / Graft Copolymer / Molecular Recognition / Functional Polymer / alpha-Amino Acid N-Carboxyanhydride (NCA) / 糖ペプチド / 細胞認識 / アミノ酸N-カルボキシ無水物 / 糖鎖高分子 / レクチン / N-アセチルグルコサミン
Research Abstract

Well-defined glycopeptide-containing block copolymers were synthesized by ring-opening polymerization of a sugar-substituted alpha-amino acid N-carboxyanhydride (NCA), i.e., O-(tetra-O-acetyl-beta-D-gluco-pyranosyl)-L-serine NCA (1), initiated with omega-amine-terminated poly (2-methyl-2-oxazoline) and poly (2-phenyl-2-oxazoline) macroinitiators in dichloromethane at 27゚C.DPs of peptide segments of the resulting poly (2-methyl-2-oxazoline)-block-poly [O-(tetra-O-acetyl-beta-D-glucopyranosyl)-L-serine](2a) and poly (2-phenyl-2-oxazoline)-block-poly [O-(tetra-O-acetyl-beta-D-glucopyranosyl)-L-serine](2b) were close to monomer/macroinitiator feed molar ratios. Glycopeptide-bearing block copolymers, poly (2-methyl-2-oxazoline)-block-poly [O-(beta-D-glucopyranosyl)-L-serine] and poly (2-phenyl-2-oxazoline)-block-poly [O-(beta-D-glucopyranosyl)-L-serine], were derived from 2a and 2b, respectively, by deacetylation with hydrazine monohydrate.
First synthesis of well-defined glycopeptide macromonomers with an alpha-styryl group was performed by living ring-opening polymerization of sugar-substituted NCAs, i.e., 1 and O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-L-serine NCA,followed by deacetylation with hydrazine monohydrate in methanol at 0゚C.Water-soluble copolymer between the macromonomer and acrylamide was obtained by the radical copolymerization with 2,2'-azobis (2-amidinopropane) dihydrochloride (AAPD) as an initiator in water at 55゚C.

Report

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

    (22 results)

All Other

All Publications (22 results)

  • [Publications] K. Aoi: "First Synthesis of Glycopeptide Macromonomers and Graft-Type Sugar-Containing Polymers with Glycopeptide Side Chains" Macromolecules. 29(12). 4456-4458 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K. Naka: "Aggregate of Peptide-Containing Block Copolymer with Lipase" Macromolecular Rapid Communication. 17(4). 269-274 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K. Naka: "Aggregates of Peptide-Containing Block Copolymers and their Interactions with Lipase in Aqueous Solution" Macromolecular Chemistry and Physics. 198(1). 89-100 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 岡田鉦彦: "球状糖鎖高分子シュガ-ボールの合成と応用" バイオインダストリー. 13(8). 42-50 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M. Okada: "Glycoproteins (Synthesis by NCA Method)" Polymeric Materials Encyclopedia, CRC Press, 9218 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Aoi: "First Synthesis of Glycopeptide Macromonomers and Graft- Type Sugar-Containing Polymers with Glycopeptide Side Chains" Macromolecules. 29(12). 4456-4458 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Naka: "Aggregate of Peptide-Containing Block Copolymer with Lipase" Macromolecular Rapid Communication. 17(4). 269-274 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Naka: "Aggregate of Peptide-Containing Block Copolymer and their Interactions with Lipase in Aqueous Solution" Macromolecular Chemistry and Physics. 198(1). 89-100 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Okada: Glycoproteins (Synthesis by NCA Method). Polymeric Materials Encyclopedia, 9218 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Aoi: "First Synthesis of Glycopeptide Macromonomers and Graft-Type Sugar-Containing Polymers with Glycopeptide Side Chains" Macromolecules. 29(12). 4456-4458 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] K.Naka: "Aggregate of Peptide-Containing Block Copolymer with Lipase" Macromolecular Rapid Communicaiton. 17(4). 269-274 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] K.Naka: "Aggregates of Peptide-Containing Block Copolymers and their Interactions with Lipase in Aqueous Solution" Macromolecular Chemistry and Physics. 198(1). 89-100 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] 岡田鉦彦: "球状糖鎖高分子シュガ-ボールの合成と応用" バイオインダストリー. 13(8). 42-50 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] M.Okada: "Glycoproteins (Synthesis by NCA Method)" Polymeric Materials Encyclopedia CRC Press, 9218 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Aoi,K.et al.: "Globular Carbohydrate Polymers“Sugar Balls".l.Synthesis of Novel Sugar-Persubstituted Poly(amido amine)Dendrimers." Macromolecules. 28. 5391-5393 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Aoi,K.et al.: "Miscibility of Poly(vinyl chloride)with Chitin Derivatives Having Poly(2-methyl-2-oxazoline)Side Chains." Macromolecular Rapid Communication. 16. 53-58 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Okada,M.et al.: "Synthesis of Sugar-Containing Macromonomers by Living Ring-Opening Polymerization." Macromolecular Reports. A32. 907-914 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Tsutsumiuchi,K.et al.: "Synthesis of Novel Glycopeptide-Polyoxazoline Block Copolymers by Direct Coupling between Living Anionic and Cationic Polymerization Systems." Macromolecular Rapid Communication. 16. 749-755 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Aoi,K.et al.: "New Chitin-Based Polymer Hybrids,l.Miscibility of Poly(vinyl alcohol)with Chitin Derivatives." Macromolecular Rapid Communication. 16. 757-761 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Naka,K.et al.: "Aggregate of Peptide-ContainingBlock Copolymer with Lipase." Macromolecular Rapid Communication. 17(印刷中). (1996)

    • Related Report
      1995 Annual Research Report
  • [Publications] Aoi,K.et al.: "“Poly(alkylenimine)s"in“The Polymeric Materials Encyclopedia"(共著)" Ed.by Salamone,J.C.,CRC Press,Inc.,Boca Raton,FL.U.S.A.,(in press),

    • Related Report
      1995 Annual Research Report
  • [Publications] 岡田鉦彦: "“高分子反応I、II",「高分子合成化学」,第11章、第12章" 山下雄也 編,東京電機大学出版局(共著), 289-338 (1995)

    • Related Report
      1995 Annual Research Report

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

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