Streptomycin chemistry

Streptomycin, chemistry of, 3, 337-384 Structural chemistry, of fungal polysaccharides, 23, 367-417 of the hemicelluloses, 14, 429-468 Structure, molecular, of cellulose, 19, 219-246 of dextran, 15, 341-369 of glycogens, 12, 261-298 of polysaccharide gels and networks,... 

Streptose is the first branched-chain sugar to have been identified as a component of a biological compound produced by a microorganism. This dicarbonyl sugar is known only in its derivatives. The chemistry of streptose and streptomycin has been lucidly reviewed by Lemieux and Wolfrom.1 In this article, it was noted that streptose must be either 5-deoxy-3-C -formyl-L-ribose or 5-deoxy-3-C-formyl-L-lyxose. Since then, the presence of the latter configuration (XXXIV) has been definitely established by Wolfrom and DeWalt,66 who found that N-acetyltetrahydrostreptobi-... 

Reductive desulfurization with Raney nickel of the mercaptolysis products of streptomycin has supplied one of the keys to the elucidation of the structure and configuration of that antibiotic. Since the chemistry of streptomycin has recently been reviewed37 the reactions discussed here will be considered solely as examples of hydrogenolysis and their bearing upon the problem of the structure and configuration of streptomycin will be ignored. 

Karl MyrbAck, Products of the Enzymic Degradation of Starch and Glycogen 252 M. Stacey and P. W. Kent, The Polysaccharides of Mycobacterium tuberculosis 311 R. U. Lemieux and M. L. Wolfrom, The Chemistry of Streptomycin. 337... 

Lederer, E., Glycnlipids of Acid-fast Bacteria, 16, 207-238 Lemieux, R. U., Some Implications in Carbohydrate Chemistry of Theories Relating to the Mechanisms of Replacement Reactions, 9, 1-57 Lemieux, R, U., and Wolfrom, M. L., The Chemistry of Streptomycin, 3, 337-384... 

The life and work of one of the greatest carbohydrate scientists of our time, Raymond U. Lemieux, is recalled here in a sensitive account by Bundle (Edmonton). During a remarkably productive career extending over more than half a century, Lemieux pioneered the application of NMR spectroscopy in chemistry, developed rational approaches for glycosidic coupling, made major contributions to our understanding of three-dimensional carbohydrate structures and protein binding, and made important contributions in the biomedical area. His own articles in these Advances include the chemistry of streptomycin in Volume 3, the mechanisms of replacement reactions in Volume 9, and in Volume 50 a consideration of Emil Fischer s lock and key concept of enzyme specificity. 

Our second example is from the chemistry of microorganisms. The antibiotic streptomycin is produced rather erratically by the microorganism Streptomyces griseus. It has now been discovered that another compound, called A-factor stimulates the microorganism into streptomycin production. Synthetic A-factor can be used to switch on antibiotic synthesis in the microorganism,... 

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