Chemistry of aminoglycoside

D. H. R. Barton and R. Subramanian, Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 7. Conversion of thiocarbonates into deoxy-sugars, J. Chem. Soc. Perkin Tram. 7 1718 (1977). 

In connection with the chemistry of aminoglycoside antibiotics, it was important to have a radical reaction that... 

Reviews by Hanessian et al. [20], Umezawa [21], and Cox et al. [22] deal with the chemistry of aminoglycosides Price [23] has reviewed structure-activity relationships, and Umezawa et al. [24,25] have discussed the structure, synthesis, and biosynthesis of aminoglycoside antibiotics. This chapter summarizes what is known of the stmctural classes of aminoglycosides to date and presents state-of-the-art knowledge of the mechaiusms for manifestation of the biological activities of these versatile antimicrobials. 

The Barton-McCombie deoxygenation reaction was invented for use in the manipulation of aminoglycoside antibiotics. It has become a popular method because of the mild conditions employed. Radical reactions have advantages over ionic reactions for carbohydrate chemistry. In this context, there is little neighboring group interference in cationic reactions and little elimination compared with normal nucleophilic displacement reactions. 

The discovery of Gentamydn and its successful utilisation for the treatment of serious gram-negative infections has contributed in the last years to increasing clinical use and to a rapid development of the chemistry and biochemistry of aminoglycoside antibiotics. Also of importance in the further exploration of this class of compounds are the new chemical and physico-chemical methods, e.g. H- and C-NMR-spectroscopy, mass spectroscopy. X-ray analysis and the different chromatographic methods. Synthetic efforts and studies of the inactivation mechanism have provided a preliminary insight into the relationship between structure and activity. 

There are already several comprehensive reviews of the chemical, biochemical and medicinal aspects of aminoglycosides This report mainly describes the progress made in chemistry and medicinal chemistry since 1970. Previous work will be discussed only when it appears necessary for better understanding. 

Excellent reviews of aminoglycoside antibiotics - have appeared. The chemistry of individual sugars present in this kind of antibiotic has been reviewed, - along with that of sugars contained in other kinds of antibiotics. Because the last article on aminoglycoside antibiotics that ap-... 

The mechanisms of inactivation of aminoglycoside antibiotics by resistant organisms, and die chemistry of the inactivated products, are described in Chapter 4 of this Volume (see p. 183). 

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