Viomycin. Part II. The structure of the chromophore

Abstract

The chromophoric unit of viomycin is shown to be the monoureide of C-formylglycine, which is present in peptide combination. Hydrogenolysis of viomycin followed by hydrolysis yields alanine, which is not present in viomycin hydrolysates and which is derived from the chromophore. Other reactions of viomycin which involve the chromophore are discussed. The rate of evolution of urea during mild hydrolyses of viomycin is shown to correspond to the rate of loss of the chromophore; the unstable product, deureidoviomycin, can be recombined with urea to reconstitute the antibiotic.