Puckering effects of 4-hy-droxy-l-proline isomers on the conformation of ornithine-free Gramicidin S.

ABSTRACT: The cyclic peptide cyclo(Val-Leu-Leu-d-Phe-Pro)₂ (peptide 1) was specifically designed for structural chemistry investigations, drawing inspiration from Gramicidin S (GS). Previous studies have shown that Pro residues within 1 adopt a down-puckering conformation of the pyrrolidine ring. By incorporating fluoride-Pro with 4-trans/cis-isomers into 1, an up-puckering conformation was successfully induced. In the current investigation, introducing hy-droxy-prolines with 4-trans/cis-isomer configurations (tHyp/cHyp) into 1 gave cyclo(Val-Leu-Leu-d-Phe-tHyp)₂ methanol disolvate monohydrate, C₆₂H₉₄N₁₀O₁₂·2CH₄O·H₂O (4), and cyclo

SUBMITTER: Asano A 

PROVIDER: S-EPMC11389682 | biostudies-literature | 2024 Sep

REPOSITORIES: biostudies-literature