Chemical studies on tuberactinomycin. VIII. Isolation of tuberactinamine N, the cyclic peptide moiety of tuberactinomycin N, and conversion of tuberactinomycin N to O.

Abstract

Tuberactinamine N, the cyclic peptide moiety of tuberactinomycin N, was obtained in a crystalline state through liberation of gamma-hydroxy-beta-lysine from tuberactinomycin N by acid treatment. Tuberactinamine N possesses an intramolecular hydrogen bond in its molecule and showed antibacterial activities comparable to those of the original antibiotics. Conversion of tuberactinomycin N to O was achieved through coupling of diacyl-beta-lysine with tuberactinamine N followed by removal of the protecting groups.