• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to project page

2007 Fiscal Year Final Research Report Summary

Structure and Function of chiral Helical Foldamers Constructed by Three-Centered Hydrogen Bonding

Research Project

Project/Area Number 18550117
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional materials chemistry
Research InstitutionChiba University

Principal Investigator

AKAZOME Motohiro  Chiba University, Faculty of Engineering, Associate Professor (10261934)

Project Period (FY) 2006 – 2007
KeywordsPeptide Chemistry / Three-centered hydrogen bond / Supramolecular Chemistry / Foldamer
Research Abstract

We have found the 2-aminophenoxyacetic acid oligomer constructs 2-fold helical structure by three-centered hydrogen-bond. When the N-terminus of the oligomer has a nitro group, their different chromophores complicate the UV and CD spectra of their oligomers. In this context, we transformed the nitro group of oligomers into the spectroscopically-resembling methoxyactamide moiety so as to easily characterize the folding structure by the UV and CD spectra. On the UV spectra in cyclohexane, the tetramer showed hypochromic effect caused by stacking of benzene rings. Here, we characterized the chiral helical structure as new functionalized foldmers. 1. Synthesis and characterization of foldamers having different side chains: As seen in leucine zipper protein, intermolecular interactions between isobutyl groups may form bundle of alpha-helix. The spectra of foldamer having isobutyl group are similar to that of methyl group. On their H-NMR spectra, up-field shift of two terminal methyl groups of isobutyl group was observed. Since no evidence to form bundle of helical structure was found, additional molecular interaction such as hydrophobic interactions will be required to form a bundle of foldamers. 2. In the above conjunction, we found that cyclic trimers of 3-aminophenoxyactic acids construct a bowl-shaped structure, which was not affected by solvents and their side chains.

  • Research Products

    (8 results)

All 2008 2007

All Journal Article (4 results) (of which Peer Reviewed: 2 results) Presentation (4 results)

  • [Journal Article] Induced Helix of 2-(2-Aminophenoxy) alkanoic Acid Oligomers as a δ-Peptidomimetic Foldamer2008

    • Author(s)
      M. Akazome, Y. Ishii, T. Nireki, and K. Ogura
    • Journal Title

      Tetrahedron Letters (印刷中)

    • Description
      「研究成果報告書概要(和文)」より
    • Peer Reviewed
  • [Journal Article] Induced Helix of 2-(2-Aminophenoxy) alkanoic Acid Oligomers as a d-Peptidomimetic Foldamer2008

    • Author(s)
      M. Akazome, Y. Ishii, T. Nireki, and K. Ogura
    • Journal Title

      Tetrahedron Letters (in press)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Inclusion compounds of L,D-dipeptide with small sulfoxides: flexible sheet structure of (S)-phenylglycyl-(R)-phenylglycine2007

    • Author(s)
      M. Akazome, A. Hirabayashi, K. Senda and K. Ogura
    • Journal Title

      Tetrahedron 60

      Pages: 9933-9938

    • Description
      「研究成果報告書概要(和文)」より
    • Peer Reviewed
  • [Journal Article] Inclusion compounds of L, D-dipeptide with small sulfoxides: flexible sheet structure of (S)-phenylglycyl-(R)-phenylglycine2007

    • Author(s)
      M. Akazome, A. Hirabayashi, K. Senda and K. Ogura
    • Journal Title

      Tetrahedron 60

      Pages: 9933-9938

    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] 2-アミノフェノキシ酢酸からなるペプチドミメティックホルダマーの側鎖がらせん構造に及ぼす影響2008

    • Author(s)
      赤染元浩, 後藤洋平, 小倉克之
    • Organizer
      日本化学会第88春季年会, 1K1-35
    • Place of Presentation
      立教大学(東京都)
    • Year and Date
      2008-03-26
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] 側鎖の異なる3-アミノフェノキシ酢酸誘導体を含む環状ペプチドミメティック分子の合成と分子構造2008

    • Author(s)
      赤染元浩, 柳生大輔, 小倉克之
    • Organizer
      日本化学会第88春季年会, 1K1-35
    • Place of Presentation
      立教大学(東京都)
    • Year and Date
      2008-03-26
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Synthesis and Structure of Cyclic Peptides Consisted of 3-Aminophenoxyacetic Acid Having Different Side Chains2007

    • Author(s)
      M. Akazome, Y. Goto, K. Ogura
    • Organizer
      88th Annual Meeting of Japan Chemical Society
    • Place of Presentation
      Rikkyo University (Tokyo)
    • Year and Date
      2007-03-27
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] Peptidomimetic Foldamers of Aminophenoxyacetic Acid Units: Effect of Side Chains on the Helical Structure2007

    • Author(s)
      M. Akazome, Y. Goto, K. Ogura
    • Organizer
      88th Annual Meeting of Japan Chemical Society
    • Place of Presentation
      Rikkyo University (Tokyo)
    • Year and Date
      2007-03-27
    • Description
      「研究成果報告書概要(欧文)」より

URL: 

Published: 2010-02-04  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi