Milton D. Yudis

The gentamicin antibiotics. Part II. Separation and degradation of the gentamicin C components. The purpurosamines, a new class of naturally occurring 2,6-diaminomonosaccharides

Separation of the gentamicin C components by column chromatography and subsequent mercaptolysis of their per-N-acetyl derivatives has permitted the isolation of derivatives of three new amino-sugars named purpurosamine A, B and C corresponding to gentamicins C1, C2a, and C1a respectively. The purpurosamines are shown to be members of the 2,6-diamino-2,3,4,6-tetradeoxyhexose family, a new class of naturally occurring monosaccharides.

The gentamicin antibiotics. Part I. Structure and absolute stereochemistry of methyl garosaminide

Methanolysis of the gentamicin C complex gave the anomeric methyl glycosides of a monosaccharide (named garosamine) shown to be methyl 3-deoxy-4-C-methyl-3-methylamino-L-arabinopyranoside (III).

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

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.