Deoxy-thio sugars

There exist many naturally occurring sugars in which a hydroxyl group of a monosaccharide is replaced by an amino or a thiol group. These compounds, commonly called amino or thio sugars, play a wide variety of important biological roles. Representative examples of these classes are 2-acetamido-2-deoxy-a-D-glucose (1) and 7-(5-S-methyl-5-thio-/ -D-ri-bosyl)adenine (vitamin L2,2). The former is the product of hydrolysis of... 

Horton, D., Tables of Properties of 2-Amino-2-deoxy Sugars and Their Derivatives, 16, 159-200 Horton, D., and Hutson, D. H., Developments in the Chemistry of Thio Sugars, 18, 123-199 Horton, D. See also, Foster, A. B. Hough, L., and Jones, J. K. N., The Biosynthesis of the Monosaccharides,... 

Thio sugars. See Sugars, deoxy-thio-. Tracers,... 

Thio sugar synthesis by this route involves sulfur as the attacking group X, and, again, the greatest success has been achieved when Y is an amino group, as in the synthesis of methyl 3-amino-3-deoxy-2-thio-a-D-allo-pyranoside (114). Methyl 3-amino-4,0-O-benzylidene-3-deoxy-a-D-altro-pyranoside was converted to the 2-0-(methylsulfonyl)-3-iV-[(methylthio)-thiocarbonyl] derivative (110), which was cyclized in boiling pyridine. 

The yeast nucleoside containing a thio sugar has been shown to be 6-amino-9-(5-d-methyl-5-thio-D-ribofuranosyl)-9i/-purine []5-deoxy-5-(methyIthio)adenosine] (130). 

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