Studies on Antibiotics and Related Substances. VII. The Structure of Kanamycin

Evidence is presented to show that both the two aminohexose moieties in kanamycin are directly joined to deoxystreptamine through hydroxyl groups by glucosidic linkages. Proof for the sites of attachment of the two aminohexose moieties rests on the periodate oxidation of the optically inactive 1,3-diamino-4,6-dihydroxy-5-methoxycyclohexane and its N-acetyl derivative which were obtained by the degradation of exhaustively methylated N-acetylkanamycin by acid hydrolysis followed by acetylation. Kanamycin is therefore represented by formula VII.