Synthesis of [Hexafluorovalyl^<1,1'>]gramicidin S

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Author(s)

    • ARAI Toru
    • Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of Technology
    • IMACHI Takashi
    • Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of Technology
    • KATO Tamaki
    • Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of Technology
    • OGAWA H. Iyehara
    • Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of Technology
    • FUJIMOTO Tsutomu
    • Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of Technology
    • NISHINO Norikazu
    • Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of Technology

Abstract

[Hexafluorovalyl<sup>1,1′</sup>]gramicidin S (<b>8</b>), in which two valine residues in the natural gramicidin S were replaced by <FONT SIZE="-2">L</FONT>-hexafluorovaline (Hfv) residues, was synthesized by the solid-phase-synthesis and cyclization-cleavage method on benzophenone oxime resin. Though the racemic hexafluorovaline derivative was employed for the peptide synthesis, the desired product was isolated in moderate yield, probably reflecting the stable cyclic structure of <b>8</b>. CD and <sup>1</sup>H NMR spectra indicated that the conformation of <b>8</b> is similar to that of gramicidin S. The two <i>β</i>-turn structure and antiparallel <i>β</i>-sheet structure with four intramolecular hydrogen bondings were maintained in spite of introducing the hexafluorovaline residues. The dye-release experiment from lecithin vesicle and antimacrobial activity assay also indicated that <b>8</b> showed membrane-disturbing activity like gramicidin S, although the activity of <b>8</b> was somewhat weaker than gramicidin S.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 69(5), 1383-1389, 1996-05-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008903351
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    Journal Article
  • ISSN
    00092673
  • Data Source
    CJP  CJPref  J-STAGE 
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