Abstract
Abstract Based on the β-turn preference of tetrapeptide sequences as analyzed by CD spectra of their chromophoric derivatives, 10 analogs of gramicidin S (GS) were designed and synthesized with general formula cyclo(–d-Leu1,1′–d-Lys2,2′–d-Leu3,3′–l-Pro4,4′–X5,5′–)2, where X is l-Asn, l-Ala, l-Leu, l-Phe, l-cyclohexylalanine, Gly, d-Ala, d-Leu, d-Phe, or d-cyclohexylalanine. Several analogs with high hydrophobicity showed antibiotic activity as strong as GS. CD spectra of the analogs with d-amino acid or Gly at the X position and their dinitrophenyl derivatives suggested that they have β-sheet conformation that is antipodal to that of GS.
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