Glucose 2-acetamido-2-deoxy-5-thio

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... 

Glucose, 4-amino-4-deoxy-D-, 152 —, 5-amino-5-deoxy-D-, 116 —4-amino-4,6-dideoxy-D-, 153 —, l,6-anhydro-6-thio-/3-D-, 226 —, 5,6-bis(acetamido)-5,6-dideoxy-D-, 175 —, 6-bromo-6-deoxy-D-, 268 —, 5,6-diamino-5,6-dideoxy-D-, 133 —, 1,2,3,4-tetra-0-acetyl-6-deoxy-6-thio-cyano-/3-D-, 235 —, 6-thio-D-, 226... 

Csuk, R, Glanzer, B I, A short synthesis of 2-acetamido-2-deoxy-5-thio-D-glucose and -D-mannose from 5-thio-D-glucal, J. Chem. Soc. Chem. Commun., 343-344, 1986. 

Thio-D-glucose has been demonstrated to be a substrate for lactose synthetase which converts it into 5-thio-lactose. The reaction of r/c-epoxides with thiourea to yield y/c-epithio-compounds has been used to synthesize 2-acetamido-2-deoxy-5-thio-D-glucopyranose as portrayed in Scheme 5. Two further papers on the reaction of epimines with sulphur-containing compounds have appeared (see Vol. 11, p. 97). Reactions leading to... 

An affinity column prepared from 4-aminophenyl l-thio-jS-L-fucopyranoside residues attached to agarose through succinylated 3,3 -diaminodipropylamine bridges has been shown to bind jS-D-2-acetamido-2-deoxyglucosidase from the serum of horseshoe crab (Limulus polyphemus). The enzyme was eluted by 2-acetamido-2-deoxy-D-glucose at a concentration of 2 mg ml and by other monosaccharides at higher concentrations in a form free from other glycoside hydrolases. 

---