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Synthesis of Functional Polymers Based on Amino Acids

Research Project

Project/Area Number 09650975
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 高分子合成
Research InstitutionTOKYO INSTITUTE OF TECHNOLOGY

Principal Investigator

SANDA Fumio  Tokyo Institute of Technology Research Laboratory of Resources Utilization Associate Professor, 資源化学研究所, 助教授 (70262318)

Co-Investigator(Kenkyū-buntansha) ENDO Takeshi  Tokyo Institute of Technology Research Laboratory of Resources Utilization Profe, 資源化学研究所, 教授 (40016738)
Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 1998: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1997: ¥2,100,000 (Direct Cost: ¥2,100,000)
Keywordsamino acid / peptide / functional polymer / cationicpolymerization / anionic polymerization / radical polymerization / polycondensation / polyaddition
Research Abstract

This work dealt with (1) synthesis and cat ionic polymerization of epoxides having amino acids and peptides, (2) synthesis and anionic and cationic polymerizations of cyclic carbonates having amino acids and peptides, (3) synthesis and radical polymerization of methacryl and acrylamides having amino acids and peptides, (4) polycondensation of amino acid-based diols and diamines with dicarboxylic acids, (5) amino acid-based diolefins with dithiols, and properties of the obtained polymers. (1) afforded polyethers with molecular weights of several thousands. Hydrogenation completely removed the protecting groups of the amino acid moieties to afford the corresponding polymers having amino groups in the side chains, and polypeptides formed via a reaction between the side chains. (2) afforded polycarbonates with molecular weights of ten thousand by anionic polymerization, but afforded oligomers by cationic polymerization, probably due to the occurrence of the Friedel-Craft reaction to the ar … More omatic rings in the protecting groups, and/or back-biting reaction to the polymer main chain. (3) afforded the corresponding polymethacryl and acrylamides with molecular weights of several ten thousands. The methacrylamide with a dipeptide structure showed a larger polymerizability than that with a monopeptide structure, probably due to hydrogen bonding between the peptide moieties. The polymers showed specific rotations ca. 30 degree larger in the negative direction compared with the monomers. The molecular dynamics simulation predicted that the polymers changed their conformations to decrease the steric hindrance between the side chains. (4) afforded the corresponding polyester-amides with molecular weight of ten thousand. The polymer with along main chain showed a lower glass transition temperature, where even-odd effect was observed, probably caused by hydrogen bonding between the polymer main chains. The polymers showed hydrolytic degradation in a buffer solution with pH of 7.8. (5) afforded the corresponding polyester-amide-sulfides, which showed enzymatic degradability, and were oxidized by hydrogen peroxide and m-chloroperbenzoic acid into sulfides and sulfones. Less

Report

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

    (41 results)

All Other

All Publications (41 results)

  • [Publications] F.Sanda, M.Nakamura, and T.Endo: "Solvent Effect and Molecular Orbital Study on the Specific Rotation of a Methacrylamide having L-leucine Structure in the Side Chain" Chem.Lett.175-176 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.koyama, F.Sanda, and T.Endo: "Polycondensations of Hydroxycarboxylic Acids Derived from Optically Active Aminoalcohols and Acid Anhydrides-Syntheses of Functional Poly(ester-amide)s-" J.Polym.Sci., Part A : Polym. Chem.35. 345-352 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Murata, F.Sanda, and T, Endo: "Syntheses and Radical Polymerization Behavior of Methacrylamides having Peptide Moieties : Effect of the Methylene Chain Introduced between the Methacrylamide and Peptide Moieties on the Polymerizability" Macromolecules. 30. 2902-2906 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] F.Sanda, T.Abe, and T.Endo: "Syntheses and Radical Polymerizations of Optically Active(Meth)acrylamides Having Amino Acid Moieties" J.polym.Sci., Part A : Polym.Chem.35. 2619-2629 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Koyama, F.Sanda, and T.Endo: "Polycondensations of Dicarboxylic Acids and Diols Derived from Optically Active Amino Alcohols" J.Polym.Sci., Part A :Polym.Chem.35. 2925-2934 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Koyama, F.Sanda, and T.Endo: "Syntheses and Radical Polymerizations of Methacrylamides Derived from Optically Active Amino Alcohols" macromol.Chem.Phys.198. 3699-3707 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Koyama, F.Sanda, T.Endo: "Radical Polyadditions of Dithiols with Diolefins Derived from Optically Active Amino Alcohols" Macromolecules. 31. 1495-1500 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] H.Murata, F.Sanda, T.Endo: "Synthesis and Radical Polymerization of a Novel Acrylamide Having an α-Helical Peptide Structure in the Side Chaln" J.Polym.Sci., Part A :Polym.Chem.36. 1679-1682 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] F.Sanda, F.Ogawa, T.Endo: "Syntheses of Functionalized Polymethacrylamides Based on Methionine Oxides" Polymer. 39. 5543-5547 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] F.Sanda, E.Koyama, T.Endo: "Synthesis and Reactions of a Poly(methacrylate)from an Optically Active Amino Alcohol" J.Polym.Sci., Part A :Polym.Chem.36. 1981-1986 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] F.Sanda, M.Nakamura, T.Endo: "Syntheses and Radical Polymerization Behavior of Novel Optically Active Methacrylamides Having L-Leucine Structure in the Side Chains" J.Polym.Sci, Part A :Polym.Chem.36. 2823-2825 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] F.Sanda, T.Kurokawa, T.Endo: "Synthesis, Reactions, and Electrolyte Properties of Polymethacrylamides Having L-threo-β-Hydroxyaspartic Acid Moiety" Polymer J. 31. 353-358 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Fumio Sanda, Masafumi Nakamura, and Takeshi Endo: "Solvent Effect and Molecular Orbital Study on the Specific Rotation of a Methacrylamide Having L-Leucine Structure in the Side Chain" Chem.Lett. 175-176 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Emiko Koyama, Fumio Sanda, and Takeshi Endo: "Polycondensations of Hydroxycarboxylic Acids Derived from Optically Active Aminoalcohols and Acid Anhydrides-Syntheses of Functional Poly(ester-amide)s-" J.Polym.Sci., Part A : Polym.Chem.35. 345-352 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Fumio Sanda and Takeshi Endo: "Synthesis and Cationic Polymerization of a Novel Optically Active Vinyl Ether with L-Proline Structure" Macromol.Chem.Phys.198. 1209-1216 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Hironobu Murata, Fumio Sanda, and Takeshi Endo: "Syntheses and Radical Polymerization Behavior of Methacrylamides Having Peptide Moieties : Effect of the Methylene Chain Introduced between the Methacrylamide and Peptide Moieties on the Polymerizability and Polymer Structure" Macromolecules. 30. 2902-2906 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Hironobu Murata, Fumio Sanda, and Takeshi Endo: "Synthesis and Radical Polymerization Behavior of a Novel Methacrylate Having L-Leucyl-L-alanyl-glycine Peptide Moiety" Macromol.Chem.Phys.198. 2519-2529 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Fumio Sanda, Toru Abe, and Takeshi Endo: "Syntheses and Radical Polymerizations of Optically Active(Meth)acrylamides Having Amino Acid Moieties" J.Polym.Sci., Part A : Polym.Chem.35. 2619-2629 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Emiko Koyama, Fumio Sanda, and Takeshi Endo: "Polycondensations of Dicarboxylic Acids and Diols Derived from Optically Active Amino Alcohols" J.Polym.Sci., Part A : Polym.Chem.35. 2925-2934 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Emiko Koyama, Fumio Sanda, and Takeshi Endo: "Syntheses and Radical Polymerizations of Methacrylamides Derived from Optically Active Amino Alcohols" Macromol.Chem.Phys.198. 3699-3707 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Emiko Koyama, Fumio Sanda, and Takeshi Endo: "Syntheses of Poly(ester-amide)s Derived from Optically Active Aminoalcohols" Macromol.Symp.122. 275-280 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Emiko Koyama, Fumio Sanda, and Takeshi Endo: "Radical Polyadditions of Dithiols with Diolefins Derived from Optically Active Amino Alcohols" Macromolecules. 31. 1495-1500 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Hironobu Murata, Fumio Sanda, and Takeshi Endo: "Synthesis and Radical Polymerization of a Novel Acrylamide Having an a-Helical Peptide Structure in the Side Chain" J.Polym.Sci., Part A : Polym.Chem.36. 1679-1682 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Fumio Sanda, Futoshi Ogawa, and Takeshi Endo: "Synthesis of Functionalized Polymethacrylamides Based on Methionine Oxides" Polymer. 39. 5543-5547 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Fumio Sanda, Emiko Koyama, and Takeshi Endo: "Synthesis and Reactions of a Poly(methacrylate)from an Optically Active Amino Alcohol" J.Polym.Sci., Part A : Polym.Chem.36. 1981-1986 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Fumio Sanda, Masafumi Nakamura, and Takeshi Endo: "Syntheses and Radical Polymerization Behavior of Novel Optically Active Methacrylamides Having(L)-Leucine Structure in the Side Chains" J.Polym.Sci., Part A : Polym.Chem.36. 2823-2825 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Fumio Sanda, Takashi Kurokawa, and Takeshi Endo: "Synthesis, Reactions, and Electrolyte Properties of Polymethacrylamides Having L-threo-beta-Hydroxyaspartic Acid Moiety" Polymer J.31. 353-358 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Hiroto Kudo, Fumio Sanda, and Takeshi Endo: "Syntheses and Radical Polymerization of Optically Active Monomer Derived from Cysteine" Macromol.Chem.Phys.(in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Fumio Sanda, Jun Kamatani, Hiroshi Handa, and Takeshi Endo: "Radical Polymerization Behavior of a Proline-substituted Acrylamide.Effect of s-Cis-Trans Isomerization on the Polymerization" Macromolecules. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] E.Koyama,F.Sanda,T.Endo: "Radical Polyadditions of Dithiols with Diolefins Derived from Optically Active Amino Alcohols" Macromolecules. 31. 1495-1500 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] H.Murata,F.Sanda,T.Endo: "Synthesis and Radical Polymerization of a Novel Acrylamide Having an α-Helical Peptide Structure in the Side Chain" J.Polym.Sci.,Part A:Polym.Chem.36. 1679-1682 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] F.Sanda,F.Ogawa,T.Endo: "Syntheses of Functionalized Polymethacrylamides Based on Methionine Oxides" Polymer. 39. 5543-5547 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] F.Sanda,E.Koyama,T.Endo: "Synthesis and Reactions of a Poly(methacrylate)from an Optically Active Amino Alcohol" J.Polym.Sci.,Part A: Polym.Chem.36. 1981-1986 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] F.Sanda,M.Nakamura,T.Endo: "Syntheses and Radical Polymerization Behavior of Novel Optically Active Methacrylamides Having L-Leucine Structure in the Side Chains" J.Polym.Sci.,Part A: Polym.Chem.36. 2823-2825 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] F.Sanda,T.Kurokawa,T.Endo: "Synthesis,Reactions,and Electrolyte Properties of Polymethacrylamides Having L-threo-β-Hydroxyaspartic Acid Moiety" Polymer J. 31. 353-358 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] F.Sanda, M.Nakamura, and T.Endo: "Solvent Effect and Molecular Orbital Study on the Specific Rotation of a Methacrylamide Having L-Leucine Structure in the Side Chain" Chem. Lett.175-176 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] E.Koyama, F.Sanda, and T.Endo: "Polycondensations of Hydroxycarboxylic Acids Derived from Optically Active Aminoalcohols and Acid Anihydeides-Syntheses of Functional Poly (ester-amide) s" J.Polym.Sci. : Part A : Polym.Chem.35. 345-352 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] H.Murata, F.Sanda, and T.Endo: "Syntheses and Radical Polymerization Behavior of Methacrylamides Having Peptide Moieties : Effect of the Methylene Chain Introduced between the Methacrylamide and Peptide Moieties on the Polymerizability" Macromolecules. 30. 2902-2906 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] F.Sanda, T.Abe, and T.Endo: "Syntheses and Radical Polymerizations of Optically Active (Meth) acrylamides Having Amino Acid Moities" J.Polym.Sci. : Part A : Polym.Chem.35. 2619-2629 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] E.Koyama, F.Sanda, and T.Endo: "Polycondensations of Dicarboxylic Acids and Diols Derived from Optically Active Amino Alcohols" J.Polym.Sci. : Part A : Polym.Chem.35. 2925-2934 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] E.Koyama, F.Sdnda, and T.Endo: "Syntheses and Radical Polymerizations of Methacrylamides Derived from Optically Active Amino Alcohols" Macromol.Chem.Phys.198. 3699-3707 (1997)

    • Related Report
      1997 Annual Research Report

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

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