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Chirality induction to the main chain of polymeric crown ethers and improvement in the chiral recognition ability through asymmetric cyclopolymerization

Research Project

Project/Area Number 02453103
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 高分子合成
Research InstitutionHokkaido University

Principal Investigator

YOKOTA Kazuaki  Hokakido Univ., Fac. of Eng. Professor, 工学部, 教授 (30001217)

Co-Investigator(Kenkyū-buntansha) YAMAGUCHI Kazumi  Tomakomai Nat. Coll. of Technol., Assoc. Professor, 助教授 (00133702)
TABATA Masayoshi  Hokkaido Univ., Fac. of Eng., Assoc. Professor, 工学部, 助教授 (50091476)
KAKUCHI Toyoji  Hokkaido Univ., Fac. of Eng., Instructor (80113538)
Project Period (FY) 1990 – 1992
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥6,900,000 (Direct Cost: ¥6,900,000)
Fiscal Year 1992: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1991: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1990: ¥4,500,000 (Direct Cost: ¥4,500,000)
KeywordsOptically active polymer / Chiral recognition / Molecular recognition / Cyclopolymerization / Chiral template / Ionophore / Asymmetric cyclization / Chiral induction / 光学活性クラウンポリマ- / ジビニルモノマ- / ジエポキモノマ- / 不斉制御 / 主鎖不斉 / ジベンゾクラウンポリマ- / 糖類 / ホスト・ゲスト / ジビニルエ-テル / ジエポキシド
Research Abstract

Molecular recognition of biological receptors and enzymes is concerned with their constitutional and stereochemical features. In order to use synthetic polymers for such a purpose, a recognizable structure must be more elaborately constructed. Therefore, the stereochemical control of polymer chains, in addition to the structural design of functional groups, is desired. Stereospecific polymerization, especially, asymmetric polymerization, affords one means to this end.
The polymeric chiral crown ethers containing binaphthyl and D- mannitol moieties as steric-chiral barrier, which are produced by a facile method through cyclopolymerization, are found to exhibit chiral recognition towards alpha-amino acids.
The object of this research project, therefore, is to induce the chirality to the main chain of polymeric crown ethers and to improve the ability of chiral recognition through asymmetric cyclopolymerization.
The principal results are as follows: (1) Synthesis of optically active poly(crown ether)s via cyclopolymerization of diepoxides and their chiral recognition due to the chirality of main chian. (2) Synthesis of a new acyclic ionophore through regio- and stereospecific polymerization of diepoxide derived from D-mannitol. (3) Asymmetric induction due to the chiral twist of the template through cyclopolymerization and cyclocopolymerization.

Report

(4 results)
  • 1992 Annual Research Report   Final Research Report Summary
  • 1991 Annual Research Report
  • 1990 Annual Research Report
  • Research Products

    (38 results)

All Other

All Publications (38 results)

  • [Publications] T.Kakuchi: "¨Poly chiral crown ethers,VI.Optical resolution of α-amino acid by polymers incorporating 1,3:4,6-di-O-benzylidene-D-mannitol residues¨" Polymer Journal. 22. 199-205 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 覚知 豊次: ""環化重合によるクラウンエーテル状環化ポリマーの合成とその機能"" 有機合成協会誌. 48. 1106-1114 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H.Hashimoto: "¨Synthesis of poly(dibenzo-19-crown-6) via cyclopolymerization of diepoxide¨" Polymer Bulletin. 25. 153-159 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H.Hashimoto: "¨Synthesis of a new macromolecular ionophore with 2,5-anhydro-D-glucitol units via cyclopolymerrization of 1,2:5,6-dianhydro-3,4-di-O-ethyl-D-mannitol¨" Journal of Organic Chemistry. 56. 6570-6472 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Kakuchi: "¨Sythesis of poly(hemispherand) via cyclopolymerization of diepoxide¨" Polymer Bulletin. 27. 599-605 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 横田 和明: ""光学活性ポリクラウンエーテルの合成"" 高分子. 41. 96- (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Miyajima: "¨Synthesis of polymers with cryptand-like units via radical cyclopolymerization of diacrylate and dimethacrylate derived from diaza-12-crown-4,and the binding property for lithium ion¨" Polymer Bulletin. 28. 23-28 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H.Hashimoto: "¨Polymeric chiral crown ethers,8.Synthesis of optically active poly(dibenzo-19-crown-6)s via cyclopolymerization of diepoxides¨" Macromolecules. 25. 1828-1831 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Yokota: "¨Asymmetric induction arising from the chiral twist of 2,2'-binaphthyl template in the cyclopolymerization of divinyl ethers¨" Die Makromolekulare Chemie. 193. 1805-1813 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Yokota: "¨Chirality induction arising from the twist of template on the cyclopolymerization of 2,3-0-isopropylidene-1,4-di-0-methacryloyl-L-threitol with styrene¨" Die Makromolekulare Chemie,Rapid Communication. 13. 343-349 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Kakuchi: "¨Synthesis of optically active poly(methy methacrylate) by cyclopolymerization of 1,4-di-O-methacryloyl-L-threitol¨" Macromolecules. 25. 5545-5546 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Kakuchi: "¨Cyclopolymerization of divinyl ethers.Synthesis and cation-binding property of poly(crown ether)s¨" Macromolecules. 25. 4854-4858 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T. Kakuchi: "Polymeric chiral crown ethers, VI. Optical resolution of alpha-amino acid by polymers incorporating 1,3:4,6-di- O-benzylidene-D-mannitol residues" Polym. J.22. 199-205 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T. Kakuchi: "Synthesis of poly (crown ether)s via cyclopolymerization and their host property (Japanese)" J. Synth. Org. Chem., Japn.48. 11016-1114 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H. Hashimoto: "Synthesis of poly(dibenzo- 19-crown-6) via cyclopolymerization of diepoxide" Polym. Bull.25. 153-159 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H. Hashimoto: "Synthesis of a new macromolecular ionophore with 2,5-anhydro- D-glucitol units via cyclopolymerization of 1,2:5,6-dianhydro-3,4-di-O-ethyl-D- mannitol" J. Org. Chem.56. 6470-6472 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T. Kakuchi: "Synthesis of poly(hemispherand) via cyclopolymerization of diepoxide" Polym. Bull.27. 599-605 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Yokota: "Synthesis of optically active poly(crown ether)s (Japanese)" Kobunshi. 41. 96 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Miyajima: "Synthesis of polymers with cryptand-like units via radical cyclopolymerization of diacrylate and dimethacrylate derived from diazo-12- crown-4, and the binding property for lithium ion" Polym. Bull.28. 23-28 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H. Hashimoto: "Polymeric chiral crown ethers, 8. Synthesis of opticaly active poly(dibenzo-19-crown-6)s cyclopolymerization of diepoxides" Macromolecules. 25. 1828-1831 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Yokota: "Chirality induction arising from the twist of template on the cyclopolymerization of 2,3-isopropylidene- 1,4-di-O-methacryloyl-L-threitol with styrene" Macromol. Chem. Rapid Commun.13. 343-349 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Yokota: "Asymmetric induction arising from the chiral twist of 2,2'-binaphthyl template in the cyclopolymerization of divinyl ethers" Macromol. Chem.193. 1805-1813 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T. Kakuchi: "Synthesis of optically active poly(methyl methacrylate) by cyclopolymerization of 1,4-di-O-methacryloyl-L-threitol" Macromolecules. 25. 5545-5546 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T. Kakuchi: "Cyclopolymerization of diviniyl ethers. Synthesis and cation- binding property of poly(crown ether)s" Macromolecules. 25. 4854-4858 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Miyajima: "“Synthesis of polymers with cryptand-like units via radical cyclopolymerization of diacrylate and dimethacrylate derived from diaza-12-crown-4,and the binding property for lithium ion"" Polymer Bulletin. 28. 23-28 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] H.Hashimoto: "“Polymeric chiral crown ethers,8,Synthesis of optically active poly(dibenzo-19-crown-6)s via cyclopolymerization of diepoxides"" Macromolecules. 25. 1828-1831 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] K.Yokota: "“Asymmetric induction arising from the chiral twist of 2,2′-binaphthyl template in the cyclopolymerization of divinyl ethers"" Die Makromolekulare Chemie. 193. 1805-1813 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] K.Yokota: "“Chiarlity induction arising from the twist of template on the cyclopolymerization of 2,3-0-isopropylidene-1,4-di-0-methacryloyl-L-threitol with styrene"" Die Makromolekulare Chemie,Rapid Communication. 13. 343-349 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Kakuchi: "“Synthesis of optically active poly(methyl methacrylate) by cyclopolymerization of 1,4-di-0-methacryloyl-L-threitol"" Macromolecules. 25. 5545-5546 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Kakuchi: ""Cyclopolymerization of divinyl ethers.Symthesis and cationbinding property of poly(crown ether)s"" Macromolecules. 25. 4854-4858 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Kakuchi: "“Synthesis of poly(hemispherand) via cyclopolymerization of diepoxide"" Polymer Bulletin. 27. 599-605 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] 横田 和明: "“光学活性ポリクラウンエーテルの合成"" 高分子. 41. 96- (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] H.Hashimoto;T.Kakuchi;K.Yokota: "Synthesis of a New Macromolecular Ionophore with 2,5ーAnhydroーDーglucitol Units via Cyclopolymerization of 1,2:5,6ーDianhydroー3,4ーdiーOーethylーDーmannitol" J.Org.Chem.56. 6470-6472 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] H.Hashimoto;T.Kakuchi;O.Haba;K.Yokota: "Polymeric chiral crown ethers,8. Synthesis of optically active poly(dibenzoー19ーcrownー6)s via cyclopolymerization of diepoxides" Macromolecules.

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Yokota;T.Kakuchi;T.Yamamoto;T.Hasegawa;O.Haba: "Asymmetric induction arising from the chiral twist of 2,2'ーbinaphthy template in the cyclopolymerization of divinyl ethers" Makromol.Chem.

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Yokota;T.Kakuchi;K.Sakurai;Y.Iwata;H.Kawai: "Chirality induction arising from the twist of template on the cyclopolymerization of 2,3ー0ーisopropylideneー1,4ーdiー0ーmethacryloylーLーthreitol with styrene" Makromol.Chem.,Rapid Commun.

    • Related Report
      1991 Annual Research Report
  • [Publications] H.Hashimoto,T.Kakuchi,K.Yokota: "Symthesis of poly (dibenzoー19ーcrounー6) via cyclopolymerization of diepoxide" Polymer Bulletin. 25. 153-159 (1991)

    • Related Report
      1990 Annual Research Report
  • [Publications] T.Kakuchi,O.Haba,K.Yokota: "Polymeric chiral croun ethers.7.Synthesis of polymers incorporating methy glycosides of αーDーaltrose,αーDーgalactose,αーDーhalactose,αーDーglucose,and αーDーmannose residue via cyclopolymerization of divinyl ethers" Die Makromolekulare Chemie.

    • Related Report
      1990 Annual Research Report

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Published: 1990-04-01   Modified: 2016-04-21  

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