chapter  Chapter 1
21 Pages

Chemistry of the Aminoglycosides: Structure/Function Relationships

WithWilliam J. Rost

The aminoglycoside antibiotics are characterized by the inclusion of an aminocyclitol group in their structure. Aminoglycoside antibiotics are also characterized by aminosugars attached to the aminocyclitol ring in glycosidic linkage. A very large and important group of aminoglycoside antibiotics are the 4,5-disubstituted 2-deoxystreptamine derivatives. Butikacin possess an antibiotic activity similar to amikacin or kanamycin A against the aminoglycoside-susceptible bacteria. While the aminoglycoside antibiotics are effective against both Gram-positive and Gram-negative organisms, their main value is their use against Gram-negative organisms. The use of the aminoglycoside antibiotics is thus limited in practice to the Gram-negative infections. To overcome this limitation, it would be desirable to have an orally active aminoglycoside antibiotic. The aminoglycoside antibiotics are highly water soluble. Hydrolysis of the acyl group in the body would regenerate the parent aminoglycoside antibiotic. Synthetic alterations of the aminoglycoside antibiotics might produce derivatives with a lower toxicity.