The Total Structure of the Antibiotic Longicatenamycin

Abstract

The peptide antibiotic longicatenamycin produced by a Streptomyces strain S-520 is a complex mixture of several congeners. The determination of the total structure of longicatenamycin was performed on the mixture using the procedure of N-bromosuccinimide oxidation followed by EDMAN degradation. The structure of the most abundant congener of longicatenamycin can be represented as cyclo (glycyl-L-2-amino- 6-methylheptanoyl-D-valyl-D-ornithyl-threo-β-hydroxy-L-glutamyl-5-chloro-D-tryptophyl) (Fig. 1: 1=4, m=0, n=3). There are three amino acid positions in which variations are found. The antibiotic complex contains compounds in which L-2-amino-6-methylheptanoic acid is replaced with either L-2-amino-5-methylhexanoic acid or L-2-amino- 7-methyloctanoic acid; further D-valine with D-isoleucine as well as n-ornithine with D-lysine. © 1975, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved.