Conformational analysis of an active chemotactic peptide analog containing z-dehydrophbnylalanine at position 3

Abstract

Formyl-Met-Leu-Δ^Z-Phe-OMe, an analog of the chemotactic tripeptide Formyl-Met-Leu-Phe has been synthesized to evaluate the effect of substitution of α, β -dehydrophenylalanine on activity and conformation. The analog peptide shows high biological activity in stimulating superoxide production by rabbit neutrophils. An NMR analysis of the solution conformation of the Δ^Z-Phe analog, using nuclear Overhauser effects and comparisons with the corresponding saturated peptides, favours a significant population of extended backbone conformations.