THE STRUCTURE OF EFROTOMYCIN

Abstract

The antibiotic efrotomycin (I), C₅₉H₈₈N₂O₂₀, was isolated from cultures of Nocardia lactamdurans as an amorphous yellow powder. Mass spectral and NMR analyses show that the compound is a glycoside of the known antibiotic aurodox (II), C₄₄H₆₂N₂O₁₂. Ozonolysis and hydrolysis of I produced the disaccharide V, 6-deoxy-4-O-(6-deoxy-2, 4-di-O-methyl-α-L-mannopyranosyl)-3-O-methyl-β-D-allopyranose. This disaccharide is attached to the 4-hydroxyl group of the hexahydropyran substructure of aurodox via a β-linkage to C-1 of the allose.