The gentamicin antibiotics. Part III. The gross structures of the gentamicin C components

Abstract

Methanolysis of the gentamicin C components gave methyl garosaminide and the corresponding gentamines, isolated as crystalline tetra-N-acetates. The absolute stereochemistry of the 2-deoxystreptamine portion of these tetra-N-acetates was determined by a circular dichroism method. Methylation of the penta-N-acetylgentamicin C components followed by acid hydrolysis and reacetylation gave, in each case, NN′-diacetyl-2-deoxy-NN′,5-O-tri-methylstreptamine, establishing the gentamicins to be 4,6-disubstituted 2-deoxystreptamine derivatives.