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Precision Synthesis of Glycopeptide-Type Sugar Balls and Development of Their Molecular Catalyst and Molecular Recognition

Research Project

Project/Area Number 09450349
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field 高分子合成
Research InstitutionNAGOYA UNIVERSITY

Principal Investigator

OKADA Masahiko  Nagoya University, Bioagr. Sciences, Prof., 大学院・生命農学研究科, 教授 (20023103)

Co-Investigator(Kenkyū-buntansha) NOMURA Nobuyoshi  Bioagr. Sciences, Assist. Prof., 大学院・生命農学研究科, 助手 (70291408)
AOI Keigo  Bioagr. Sciences, Assoc. Prof., 大学院・生命農学研究科, 助教授 (30222467)
Project Period (FY) 1997 – 1999
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥10,400,000 (Direct Cost: ¥10,400,000)
Fiscal Year 1999: ¥1,600,000 (Direct Cost: ¥1,600,000)
Fiscal Year 1998: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1997: ¥7,300,000 (Direct Cost: ¥7,300,000)
KeywordsGlycopeptide / Dendrimer / Living polymerization / Glycopolymer / Encapsulation / Ring-opening polymerization / Molecular recognition / Amino acid N-carboxyanhydride / ブロック共重合体 / 核酸(DNA) / デンドリマ-
Research Abstract

1. Precision Synthesis of Glycopeptide-Type Sugar Balls :
An efficient synthetic method via a reaction of primary amine-terminated dendrimer with sugar derivative-substituted α-amino acid N-carboxyanhydride (NCA) was established for glycopeptide-type sugar balls of well-defined structure. A variety of glycopeptide type-sugar balls were synthesized by the reactions of poly(amido amine) dendrimers of up to the eighth generation with glucose, galactose, and N-acetylglucosamine derivative-substituted L-serine NCAs.
2. Analysis of Propagation Rate Acceleration in Radial-Growth Polymerization (RGP) :
Ring-opening polymerization of NCAs with primary anime-terminated dendrimer as an initiator was kinetically investigated by means of conductivity measurement. On the basis of the effects of solvents, substituents, temperature, and added cyano-terminated dendrimer on the propagation rate constant, it was concluded that the observed acceleration was due to the increased monomer concentration near the dendrimer surface and the enhanced collision probability arising from the radial-growth from the surface as well.
3. Evaluation of Glycopeptide-Type Sugar Balls as Biofunctional Materials :
Encapsulation of low molecular weight compounds inside glycopeptide-type sugar balls was investigated using sodium 8-anilino-1-naphthalenesulfonate (ANS) as a probe. The number of the encapsulated ANS molecules appreciably increased when poly(amido amine) dendrimer of the eighth generation was allowed to react with N-acetylglucosamine derivative-substituted NCA in dimethyl sulfoxide. Inhibition experiments of lectin-induced hemagglutination proved that the glycopeptide-type sugar balls possessed much higher molecular recognition ability than the corresponding mono- or oligosaccharides.

Report

(4 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report
  • 1997 Annual Research Report
  • Research Products

    (33 results)

All Other

All Publications (33 results)

  • [Publications] K. Aoi: "Globular Carbohydrate Macromolecule "Sugar Balls" 2. Synthesis of Mono(glycopeptide)-Persubstituted Dendrimers by Polymer Reaction with Sugar-Substituted-Amino Acid N-Carboxyanhydrides(glycoNCAs)"Macromolecular Rapid Communication. 19(1). 5-9 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T. Imae: "Small-Angle Neutron Scattering and Surface force Investigations of Poly(amino amine) Dendrimer with Hydroxyl End Groups"Langmuir. 15. 4076-4084 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Aoi: "Synthesis of a Novel Star-Shaped Dendrimer by Radical-Growth Polymerization of Sarcosine N-Carboxy-anhydride Initiated with Poly(trimethyleneimine) Dendrimer"Macromolecular Rapid Communication. 20(7). 378-382 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Tsutsumiuchi: "Globular Carbohydrate Macromolecule "Sugar Balls" 4 : Synthesis of Dendritic Nanocapsules with Molecular Recognition Sites on Periphery"Polymer Journal. 31(11). 935-941 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Aoi: "Synthesis and Assembly of Amphiphilic Tadpole-Shaped Block Copolymers Based on Poly(amino amine) Dendrimer"Polymer Journal. 31(11-2). 1071-1078 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Tsutsumiuchi: "Ion Complex Formation between Poly(amido amine) Dendrimer HCI Salt and Poly(L-glutaminic acid) Sodium Salt"Polymer Journal. 32(2). 107-112 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] 岡田鉦彦: "シュガーボール"機能性超分子の設計と将来展望,シーエムシー. 263 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] 青井啓悟: "デンドリマーの超分子組織化を基盤とする機能材料の分子設計"新しい自己組織化ポリマー表面の解析及び機能設計,シーエムシー. 247 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Aoi, K. Tsutsumiuchi, A. Yamamoto, M. Okada: "Globular Carbohydrate macromoleclue "Sugar Balls" 2. Synthesis of Mono (glycopeptide)-persubstituted Dendrimers by Polymer Reaction with Sugar-Substituted α-Amino Acid N-Carboxyanhydrides (GlycoNCAs)"Macromol. Rapid Commun.. 19. 5-9 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T. Imae, K. Funayama, K. Aoi, K. Tsutsumiuchi, M. Okada, M. Furusaka: "Small-Angle Neutron Scattering and Surface force Investigations of Poly(amido amine) Dendrimer with Hydroxyl End Groups"Langmuir. 15. 4076-4084 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Aoi, T. Hatanaka, K. Tsutsumiuchi, M. Okada, T. Imae: "Synthesis of a Novel Star-Shaped Dendrimer by Radial-Growth Polymerization of Sarcosine N-Carboxyanhydride Initiated with Poly (trimethyleneimine) Dendrimer"Macromol. Rapid Commun.. 20 (7). 378-382 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Tsutsumiuchi, K. Aoi, M. Okada: "Globular Carbohydrate Macromolecule "Sugar Balls" 4 : Synthesis of Dendritic Nanocapsules with Molecular recognition Sites on Periphery"Polym. J.. 31 (11). 935-941 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Aoi, A. Motoda, M. Ohno, K. Tsutsumiuchi, M. Okada, T. Imae: "Synthesis and Assembly of Amphiphilic Tadpole-Shaped Block Copolymers Based on Poly(amino amine) Dendrimer"Polym. J.. 31 (11-2). 1071-1078 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Tsutsumiuchi, K. Aoi, M. Okada: "Ion Complex Formation between Poly(amido amine) Dendrimer HCl Salt and Poly(L-glutaminic acid) Sodium Salt"Polym. J.. 32 (2). 107-112 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] M. Okada, K. Aoi: "Sugar Balls, in "Design and Perspectives of Fuctional Supramolecules""CMC (Tokyo). (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] K. Aoi, M. Okada: "Molecular Design of Functional Materials Based on Supramolecular Assembly of Dendrimers, in "Characterization and Functional Design of Self-Assembled Polymer Surfaces""CMC (Tokyo). (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1999 Final Research Report Summary
  • [Publications] T.Imae: "Small-Angle Neutron Scattering and Surface force Investigations of Poly(amido amine) Dendrimer with Hydroxyl End Groups."Langmuir. 15. 4076-4084 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Aoi: "Synthesis of a Novel Star-Shaped Dendrimer by Radial-Growth Polymerization of Sarcosine N-Carboxy-anhydride Initiated with Poly(trimethyleneimine) Dendrimer."Macromolecular Rapid Communication. 20(7). 378-382 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Tsutsumiuchi: "Globular Carbohydrate Macromolecule "Sugar Balls" 4: Synthesis of Dendritic Nanocapsules with Molecular Recognition Sites on Periphery."Polymer Journal. 31(11). 935-941 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Aoi: "Synthesis and Assembly of Amphiphilic Tadpole-Shaped Block Copolymers Based on Poly(amido amine) Dendrimer"Polymer Journal. 31(11-2). 1071-1078 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Tsutsumiuchi: "Ion Complex Formation between Poly(amido amine) Dendrimer HCl Salt and Poly(L-glutaminic acid) Sodium Salt."Polymer Journal. 32(2). 107-112 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Aoi: "Globular Carbobydrate Macromolecule “Sugar Balls" 2.Synthesis.of Mono(glycopentide)-Persubstituted Dendrimers by Polymer Reaction with Sugar-Substitutedα-Amino Acid N-Carboxyanhydrides(glycoNCAs)" Macromolecular Rapid Communication. 19(1). 5-9 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Imae: "Small-Angle Neutron Scattering and Surface Force Investigations of Poly (amido amine) Dendrimer with Hydroxyl End Group." Langmuir. (印刷中).

    • Related Report
      1998 Annual Research Report
  • [Publications] 青井啓悟: "デンドリマーの分子設計 -新しいナノスケールアーキテクチャーへの招待-" 現代化学. 327(6). 20-27 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 青井啓悟: "機能性デンドリマー:シュガーボール" 高分子加工. 47(6). 256-265 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 岡田鉦彦: "シュガーボール" 機能性超分子の設計と将来展望,シーエムシー, 263 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] 青井啓悟: "デンドリマーの超分子組織化を基盤とする機能材料の分子設計" 新しい自己組織化ポリマー表面の解析及び機能設計,シーエムシー, 247 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] M.Okada: "Synthesis of Glycopeptide Conjugates via Ring-Opening Polymerization of Suger-Substituted α-Amino Acid N-Carboxyanhydrides (GlycoNCAs)" Proceedings of the Japan Academy. 73B・10. 205-209 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] K.Tsutsumiuchi: "Synthesis of Polyoxazoline- (Glyco) peptide Block Copolymers by Ring-Opening Polymerization of (Suger-Substituted) α-Amino Acid N-Carboxyanhydrides with Polyoxazoline Macroinitiators" Macromolecules. 30・14. 4013-4017 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] K.Aoi: "Globular Carbohydrate Macromolecule “Sugar Balls" 2. Synthesis of Mono (Glycopeptide) -Persubstituted Dendrimers by Polymer Reaction with Sugar-Substituted α-Amino Acid N-Carboxyanhydrides (GlycoNCAs)" Macromolecular Rapid Communication. 19・1. 5-9 (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] K.Aoi: "Globular Carbohydrate Macromolecule “Sugar Balls" 3. “Radial-Growth Polymerization" of Sugar-Substituted α-Amino Acid N-Carboxyanhydrides (GlycoNCAs) with a Dendritic Initiator" Tetrahedron. 53・45. 15415-15427 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 青井啓悟: "複合糖質高分子の精密構築 -シュガ-ボールとリビング糖ペプチド-" 高分子論文集. 54・10. 649-660 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 青井啓悟: "球状高分子デンドリマ-とは" 化学と教育. 45・12. 698-699 (1997)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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