Synthesis of (Hexafluorovalyl1, 1) gramicidin S.

T Arai, T Imachi, T Kato, HI Ogawa, T Fujimoto…

Index: Arai, Toru; Imachi, Takashi; Kato, Tamaki; Ogawa, H. Iyehara; Fujimoto, Tsutomu; Nishino, Norikazu Bulletin of the Chemical Society of Japan, 1996 , vol. 69, # 5 p. 1383 - 1389

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Citation Number: 17

Abstract

[Hexafluorovalyl 1, 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 ...