The structure of hikizimycin. I. Identification of 3-amino-3-deoxy-D-glucose and cytosine as structural components

The molecular formula for hikizimycin, a new antibiotic isolated from Streptomyces A-5, is now established as C₂₁H₃₇N₅O₁₄. Evidence in support of the occurrence of 3-amino-3-deoxy-D-glucose and cytosine residues in the antibiotic molecules is presented. Methanolysis of N,N′-diacetylhikizimycin gave mainly two components. Fragment A was characterized as methyl 3-amino-3-deoxy-D-glucopyranoside by its conversion into the known methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-α-D-glucopyranoside. Fragment B, on catalytic hydrogenation followed by acid hydrolysis, gave tetrahydropyrimidin-2-one, characterized as its picrate, thus establishing the presence of a cytosine residue in hikizimycin.