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Development of Straightforward Synthetic Methods for Biologically Active Molecules Utilizing Intermolecular Interactions on Artificial Receptors

Research Project

Project/Area Number 14350474
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionTOYAMA MEDICAL AND PHARMACEUTICAL UNIVERSITY

Principal Investigator

INOUYE Masahiko  Toyama Medical and Pharmaceutical University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (60211752)

Co-Investigator(Kenkyū-buntansha) FUJIMOTO Kazuhisa  Toyama Medical and Pharmaceutical University, Faculty of Pharmaceutical Sciences, Research Associate, 薬学部, 助手 (40334718)
ABE Hajime  Toyama Medical and Pharmaceutical University, Faculty of Pharmaceutical Sciences, Research Associate, 薬学部, 助手 (10324055)
Project Period (FY) 2002 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥14,500,000 (Direct Cost: ¥14,500,000)
Fiscal Year 2004: ¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 2003: ¥3,300,000 (Direct Cost: ¥3,300,000)
Fiscal Year 2002: ¥7,900,000 (Direct Cost: ¥7,900,000)
KeywordsArtificial Receptor / Molecular Recognition / Saccharide / Ethynylpyridine / Chiral Helix / Hydrogen-Bonding / Higher-Order Structure / Artificial Enzyme / 人工ホスト分子 / 核酸塩基 / ポリピリジン / ジアミドピリジン / ピレノファン
Research Abstract

During the last four decades, organic synthesis has been progressing explosively, whereas selective reaction of complexed and highly hydrophilic molecules is not easy. Thus, in practical synthesis of such molecules, the use of protection groups is essential for achieving the synthetic transformations.
The final aim of this research project is to develop novel straightforward synthetic methods for biologically active molecules utilizing intermolecular interactions on artificial receptors. With this goal in mind, we firstly designed and synthesized artificial receptors that selectively recognize such biomolecules. Next, we tried to obtain basic information of the artificial receptors for applying them to organic transformations of the bound molecules.
The results obtained in this research project are as follows :
1)We synthesized poly(ethynylpridine)s, in which the pseudelinear conformation of the polymer is guided to a well-ordered helical and chiral structure upon recognition of saccharide derivatives in aprotic solvents.
2)We characterized the chiral helices of the polymer described above on the basis of various spectroscopic methods such as ultra-violet absorption, fluorescence emission, and circular dichroism.
3)We also synthesized water-soluble poly(ethynylpyrdine)s by functionalizing side chains of the hydrophobic ones and characterized their higher-order structures.
4)Transformation of the bound saccharides was studied, and we obtained various informations for them.

Report

(4 results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • 2002 Annual Research Report
  • Research Products

    (29 results)

All 2005 2004 2003 Other

All Journal Article (13 results) Book (2 results) Patent(Industrial Property Rights) (4 results) Publications (10 results)

  • [Journal Article] Tautomeric Self-Dimerization and Molecular Recognition Properties of 2-Aminopyrimidinone Derivatives as Triple Hydrogen-Bonding Modules in Molecular Assemblies2005

    • Author(s)
      Hajime Abe
    • Journal Title

      European Journal of Organic Chemistry (in press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Journal Article] A Rigid C_<3v>-Symmetrical Host for Saccharide Recognition: 1,3,5-Tris(2-hydroxyaryl)-2,4,6-trimethylbenzenes2005

    • Author(s)
      Hajime Abe
    • Journal Title

      Organic Letters 7

      Pages: 59-61

    • Related Report
      2004 Annual Research Report
  • [Journal Article] A Rigid C_<3v>-Symmetrical Host for Saccharide Recognition : 1,3,5-Tris(2-hydroxyaryl)-2,4,6-trimethylbenzenes2004

    • Author(s)
      Hajime Abe
    • Journal Title

      Organic Letters 7

      Pages: 59-61

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Effective Stabilisation of α-Helical Structures in Short Peptides with Acetylenic Cross-Linking Agents2004

    • Author(s)
      Kazuhisa Fujimoto
    • Journal Title

      Chemical Communication

      Pages: 1280-1281

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Saccharide-Dependent Induction of Chiral Helicity in Achiral Synthetic Hydrogen-Bonding Oligomers2004

    • Author(s)
      Masahiko Inouye
    • Journal Title

      Journal of the American Chemical Society 126

      Pages: 2022-2027

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Journal Article] Unambiguous Detection of Target DNAs by Excimer-Monomer Switching Molecular Beacons2004

    • Author(s)
      Kazuhisa Fujimoto
    • Journal Title

      The Journal of Organic Chemistry 69

      Pages: 3271-3275

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Journal Article] Synthesis and Molecular Recognition of Pyrenophanes with Polycationic or Amphiphilic Functionalities : Artificial Plate-Shaped Cavitant Incorporating Arenes and Nucleotides in Water2004

    • Author(s)
      Hajime Abe
    • Journal Title

      The Journal of Organic Chemistry 69

      Pages: 495-504

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Journal Article] Unambiguous Detection of Target DNAS by Excimer-Monomer Switching Molecular Beacons2004

    • Author(s)
      Kazuhisa Fujimoto
    • Journal Title

      The Journal of Organic Chemistry 69

      Pages: 3271-3275

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Effective Stabilisation of alpha-Helical Structures in Short Peptides with Acetylenic Cross-Linking Agents2004

    • Author(s)
      Kazuhisa Fujimoto
    • Journal Title

      Chemical Communication

      Pages: 1280-1281

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Highly Efficient Recognition of Native TpT by Artificial Ditopic Hydrogen-Bonding Receptors Possessing a Conformationally Well-Defined Linkage2003

    • Author(s)
      Masayoshi Takase
    • Journal Title

      The Journal of Organic Chemistry 68

      Pages: 1134-1137

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Stereoselective Synthesis of Alkynyl C-2-Deoxy-β-D-ribofuranosides via Intramolecular Nicholas Reaction : A Versatile Building Block for Non-natural C-Nucleosides2003

    • Author(s)
      Masayoshi Takase
    • Journal Title

      Organic Letters 5

      Pages: 625-628

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] 疎水性ポケット分子によるヌクレオチド認識の現状と将来(総説)2003

    • Author(s)
      阿部 肇
    • Journal Title

      未来材料 3

      Pages: 28-34

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Recent Research Developments in Organic Chemistry Vol.72003

    • Author(s)
      Masahiko Inouye
    • Journal Title

      Transworld Research Network

      Pages: 13-13

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Book] 第5版 実験化学講座13「有機化合物の合成I」2004

    • Author(s)
      井上 将彦
    • Total Pages
      26
    • Publisher
      丸善
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Book] Recent Research Developments in Organic Chemistry Vol. 72003

    • Author(s)
      Masahiko Inouye
    • Total Pages
      13
    • Publisher
      Transworld Research Network
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 特許2005

    • Inventor(s)
      井上 将彦, 藤本 和久, 清水 久夫
    • Industrial Property Rights Holder
      国立大学法人富山医科薬科大学
    • Industrial Property Number
      2005-118313
    • Filing Date
      2005-04-15
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 特許2004

    • Inventor(s)
      井上 将彦, 千葉 順哉, 池田 怜男奈, 高瀬 雅祥
    • Industrial Property Rights Holder
      独立行政法人科学技術振興機構
    • Industrial Property Number
      2004-293332
    • Filing Date
      2004-10-06
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 特許2004

    • Inventor(s)
      井上 将彦, 藤本 和久, 清水 久夫
    • Industrial Property Rights Holder
      国立大学法人富山医科薬科大学
    • Industrial Property Number
      2004-315018
    • Filing Date
      2004-10-29
    • Related Report
      2004 Annual Research Report
  • [Patent(Industrial Property Rights)] 特許2003

    • Inventor(s)
      井上 将彦, 藤本 和久, 清水 久夫
    • Industrial Property Rights Holder
      独立行政法人科学技術振興機構
    • Industrial Property Number
      2003-320311
    • Filing Date
      2003-09-11
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Publications] Takase, M.: "Stereoselective Synthesis of Alkynyl C-2-Deoxy-β-D-ribofuranosides via Intramolecular Nicholas Reaction : A Versatile Building Block for Non-natural C-Nucleosides"Org.Lett.. 5. 625-628 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Takase, M.: "Highly Efficient Recognition of Native TpT by Artificial Ditopic Hydrogen-Bonding Receptors Possessing a Conformationally Well-Defined Linkage"J.Org.Chem.. 68. 1134-1137 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Abe, H.: "Synthesis and Molecular Recognition of Pyrenophanes with Polycationic or Amphiphilic Functionalities : Artificial Plate-Shaped Cavitant Incorporating Arenes and Nucleotides in Water"J.Org.Chem.. 69. 495-504 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Inouye, M.: "Saccharide-Dependent Induction of Chiral Helicity in Achiral Synthetic Hydrogen-Bonding Oligomers"J.Am.Chem.Soc.. 126. 2022-2027 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Fujimoto, K.: "Unambiguous Detection of Target DNAs by Excimer-Monomer Switching Molecular Beacons"J.Org.Chem.. 69(in press). (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] 阿部 肇: "ヌクレオチド認識の現状と将來(総説)"未来材料. 3. 28-34 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Inouye, M.: "Recent Research Developments in Organic Chemistry, Vol. 7"Transworld Research Network. 13 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Masayoshi Takase, Masahiko Inouye: "Highly Efficient Recognition of Native TpT by Artificial Ditopic Hydrogen-Bonding Receptors Possesing a Conformationally Well-Defined Linkage"The Journal of Organic Chemistry. 68. 1134-1137 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Masayoshi Takase, Tomoyuki Morikawa, Hajime Abe, Masahiko Inouye: "Stereoselective Synthesis of Alkynyl C-2-Deoxy-β-D-ribofuranosides via Intramolecular Nicholas Reaction : A Versatile Building Block for Non-natural C-Nucleosides"Organic Letters. 5. 625-628 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] 井上将彦, 阿部肇: "先端化学シリーズIII 分子認識化学 人工ホストからバイオまで パート3-1 保護基のいらない有機合成を目指して"丸善株式会社(印刷中). (2003)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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