Conformational studies of chemotactic HCO-Met-Leu-Phe-OMe analogues

G Vertuani; M Boggian; A Breveglieri; G Cavicchioni; S Spisani; A Scatturin

doi:10.1007/BF00807274

Conformational studies of chemotactic HCO-Met-Leu-Phe-OMe analogues

Amino Acids. 1995 Dec;9(4):375-83. doi: 10.1007/BF00807274.

Authors

G Vertuani¹, M Boggian, A Breveglieri, G Cavicchioni, S Spisani, A Scatturin

Affiliation

¹ Department of Pharmaceutical Sciences, University of Ferrara, Via Fossato di Mortara 17/19, I-44100, Ferrara, Italy.

PMID: 24178885
DOI: 10.1007/BF00807274

Abstract

In order to investigate the proper peptide backbone conformation able to elicit a biological activity, HCO-Met-Pro-Phe-OMe, HCO-Met-Ψ[COO]Leu-Phe-OMe, and HCO-Met-OLeu-Phe-OMe, analogues of the prototypical chemotactic peptide HCO-Met-Leu-Phe-OMe, were studied by CD and IR techniques. The results obtained comparing biological and conformational data evidence the critical presence of (i) the NH group at position 2, (ii) a rather flexible backbone, (iii) the chemical structure of the central residue which can affect the stability of a possible active conformer.