Peptides. Part XXIII. Experiments on the oxidation of thiostrepton

Abstract

Results from the attempted dehydrogenation of thiostrepton with manganese dioxide have not confirmed the presence of a thiazoline system in the antibiotic. Oxidation of thiostrepton with performic acid yielded 2-(1-amino-2-carboxyethyl)thiazole-4-carboxylic acid, the structure of which was proved by its further oxidation to 2-carbamoylthiazole-4-carboxylic acid, and by its reduction to aspartic acid, alanine, and glycine.