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1996 Fiscal Year Final Research Report Summary

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
KeywordsGlycopeptide / Living Polyemrization / Ring-Opening Polymerization / Block Copolymer / Graft Copolymer / Molecular Recognition / Functional Polymer / alpha-Amino Acid N-Carboxyanhydride (NCA)
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.

  • Research Products

    (9 results)

All Other

All Publications (9 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 1999-03-09  

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