The synthesis of peptide derivatives related to evolidin

Abstract

Protected peptides with amino acid sequences present in the cyclic phytopeptide evolidin have been prepared. The synthetic work involved application of the 2,4,6-trimethylbenzyl carboxyl-protecting group. Acetyl was used to mask serine side-chain hydroxyl, and high-dilution cyclization of one of the products, an O-acetyl heptapeptide p- nitrophenyl ester, gave a low yield of O-acetylevolidin, which was converted into evolidin by hydrazinolysis.