STUDIES ON NEW ANTIBIOTIC LIVIDOMYCINS. III

PARTIAL STRUCTURE OF LIVIDOMYCIN A

Abstract

The acid methanolysis of lividomycin A gave an amine, which was provisionally designated as C₁₂-amine^*, and methyl lividotriosaminide. C₁₂-Amine was degraded to 2-deoxystreptamine and an amino sugar by acid hydrolysis of the N-acetyl derivative. The chemical structure of the amino sugar was determined to be 2-amino-2, 3-dideoxy-D-glucopyranose or 3-deoxy-D-glucosamine from the NMR spectrum of peracetylated methyl glycoside of the amino sugar. An α-glycosidic linkage between 2-deoxystreptamine and 3-deoxy-Dglucosamine was shown by the NMR spectrum of N-acetyl C₁₂-amine, and N, N'-diacetyl-5, 6-di-O-methyl-2-deoxystreptamine was obtained from permethylated N-acetyl C₁₂-amine. Therefore, C₁₂-amine is 4-O-(2-amino-2, 3-dideoxy-α-D-glucopyranosyl)-1, 3-diamino-1, 2, 3-trideoxy-myo-inositol or 3'-deoxy paromamine.