Synthesis of Low-Hemolytic Antimicrobial Dehydropeptides Based on Gramicidin S
- 1 December 2006
- journal article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 49 (26) , 7592-7595
- https://doi.org/10.1021/jm061051v
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 (ΔZ3Pal) residues at the 4 and 4‘ positions (2), was synthesized by solution-phase methodologies using Boc-Leu-ΔZ3Pal azlactone. Analogue 2 exhibited high antimicrobial activity against Gram-positive bacteria and had much lower hemolytic activity than wild-type GS and the corresponding (Z)-α,β-dehydrophenylalanine (ΔZPhe) analogue (1).Keywords
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