Synthesis of [Hexafluorovalyl1,1′]gramicidin S

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  • Toru Arai
    Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of TechnologyTobata-ku, Kitakyushu 804
  • Takashi Imachi
    Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of TechnologyTobata-ku, Kitakyushu 804
  • Tamaki Kato
    Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of TechnologyTobata-ku, Kitakyushu 804
  • H Iyehara Ogawa
    Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of TechnologyTobata-ku, Kitakyushu 804
  • Tsutomu Fujimoto
    Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of TechnologyTobata-ku, Kitakyushu 804
  • Norikazu Nishino
    Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of TechnologyTobata-ku, Kitakyushu 804

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<jats:title>Abstract</jats:title> <jats:p>[Hexafluorovalyl1,1′]gramicidin S (8), in which two valine residues in the natural gramicidin S were replaced by l-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 8. CD and 1H NMR spectra indicated that the conformation of 8 is similar to that of gramicidin S. The two β-turn structure and antiparallel β-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 8 showed membrane-disturbing activity like gramicidin S, although the activity of 8 was somewhat weaker than gramicidin S.</jats:p>

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