Solid-phase synthesis of cecropin A and related peptides.

Abstract

Cecropin A, a 37-residue antibacterial peptide amide, was synthesized by the solid-phase method. It was shown to be homogeneous and totally indistinguishable from natural cecropin A by chemical and physical criteria, as well as by its antibacterial activity against several Gram-positive and Gram-negative organisms. The synthetic material was also used to establish unambiguously that the carboxyl-terminal blocking group of natural cecropin A is a primary amide as tentatively proposed earlier. The role of the amino terminus of cecropin A in antibacterial activity was investigated by the synthesis of two analogs.