Synthesis of low-hemolytic antimicrobial dehydropeptides based on gramicidin S

K Yamada, S Shinoda, H Oku, K Komagoe…

Index: Yamada, Keiichi; Shinoda, Shun-Suke; Oku, Hiroyuki; Komagoe, Keiko; Katsu, Takashi; Katakai, Ryoichi Journal of Medicinal Chemistry, 2006 , vol. 49, # 26 p. 7592 - 7595

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Citation Number: 30

Abstract

The synthesis and biological activity of a novel cyclic β-sheet-type antimicrobial dehydropeptide based on gramicidin S (GS) is described. The GS analogue, containing two (Z)-(β-3-pyridyl)-α, β-dehydroalanine (Δ Z 3Pal) residues at the 4 and 4'positions (2), was synthesized by solution-phase methodologies using Boc-Leu-Δ Z 3Pal azlactone. Analogue 2 exhibited high antimicrobial activity against Gram-positive bacteria and had much lower ...