Mannose 6-deoxy derivatives

The synthesis of a 9-azido-9-deoxy derivative of Neu5Ac, namely, 5-acetamido-9-azido-3,5,9-trideoxy-D-gh/cero-D-ga/acto -2-nomdo-pyranosonic acid, from enolpyruvate phosphate and 2-acetamido-6-azido-2,6-dideoxy-D-mannose, using Neu5Ac synthase from A. meningitidis, has been reported.225... 

I. Cerny, M. Budesinsky, T. Trnka, and M. Cerny, Preparation of 2-amino- 1,6-anhydro-2,3-dideoxy-jS-D-arabino-hexopyranose. H- and 13C-N.M.R. spectra of deoxy derivatives of 2-amino-l,6-anhydro-2-deoxy-D-glucose and 2-amino-l,6-anhydro-2-deoxy-D-mannose, Carbohydr. Res., 130 (1984) 103-114. 

The amino nitrile synthesis is particularly useful for the preparation of 2-amino-2-deoxy derivatives of rare sugars which would be difficult to obtain as intermediates in a synthesis involving animation alone. Thus, 2-amino-2-deoxy-L-glucose and 2-amino-2-deoxy-L-mannose can be prepared in good yield from the readily available L-arabinose.11,18... 

Replacement of a hydroxyl group by hydrogen yields a deoxy sugar. The derivative of ribose, deoxyribose, is a component of deoxyribonucleic acid (DNA). Similarly, deoxy derivatives of the two hexoses, galactose and mannose, occur as fucose and rhamnose, respectively, these being components of certain heteropolysaccharides. 

Deoxy-sugars. Part XXV. Structure and Reactivity of Anhydro-sugars. Part II. Derivatives of 3 6-Anhydro-D-mannose, 3 6-Anhydro-2-deoxy-D-galactose, and 3 6-Anhydro-2-deoxy-D-g ucose," A. B. Foster, W. G. Overend, M. Stacey, and G. Vaughan,/. Chem. Soc., (1954) 3367-3377. 

Nucleophilic Displacement Reactions in Carbohydrates. Part XI. Reaction of Methyl 6-Deoxy-2,3-O-isopropylidene-4-O-methyl-sulphonyl-a-L-talopyranoside with Sodium Azide A Synthesis of L-Perosamine (4-Amino-4,6-dideoxy-L-mannose) Derivatives, J. S. Brimacombe, O. A. Ching, and M. Stacey, J. Chem. Soc. C, (1969) 1270-1274. 

The incorporation and metabolism of 2-deoxy-2-fluoro-D-[ H]glucose and -D-[ H]mannose in yeast and chick-embryo cells has been studied. 2-Deoxy-2-fluoro-D-glucose, 2-deoxy-2-fluoro-D-mannose, and their GDP and UDP derivatives were found to interfere with protein (involving that of... 

As 2-amino-2-deoxy-D-mannose is tumorstatic and 2-acetamido-2-deoxy-D-mannose 6-phosphate is an obligatory intermediate in the biosynthetic pathway to sialic acid, displacement of the essential OH-6 with a fluorine atom should be interesting from the biological viewpoint. 2-Acetamido-1,3,4-tri-0-acetyl-2,6-dideoxy-6-fluoro-D-mannopyranose (see Table 111 in Section 11,3) and its O- and A,0-deacetyl derivatives were prepared the first compound showed weak anticancer activity. 

Glycosylation of Trichloroacetimidates of 2-Azido-2-deoxy-D-mannose Derivatives... 

The rate of oxidation of other monosaccharides (e.g. galactose, mannose, xylose, arabinose and fructose) by glucose oxidase has been shown to be negligible or zero but some derivatives of glucose do react slightly, e.g. 2-deoxy-D-glucose shows a reaction rate of less than 5% of that with /3-D-glucose. 

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