Studies on the synthesis of cyclic pentapeptides as LHRH antagonist and the factors that influence cyclization yield

Abstract

Six cyclic pentapeptides containing two or three non-protein amino acids have been synthesized by cyclization of linear precursors in dilute solution and characterized by TLC, HPLC, NMR, melting point, specific rotation etc. A total of 72 cyclization reactions were carried out to study the factors that influence head-to-tail cyclization: linear precursor sequence, coupling reagent, residue configuration, the proportion of DMAP additive, concentration, reaction temperature and reaction time. The cyclic pentapeptides will be modified by active moieties and evaluated as LHRH antagonists. Copyright © 2002 European Peptide Society and John Wiley & Sons, Ltd.