Deoxy Sugars

MUCHNIK DE LEDERKREMER, R; MARINO, C

Advances in Carbohydrate Chemistry and Biochemistry

Elsevier

Lugar: Amsterdam; Año: 2007; p. 143 - 216

Several deoxy sugars, notably 2-deoxy-D-erythro-pentose (2-deoxy-D-ribose) the sugar component of DNA, 6-deoxy-L-mannose (L-rhamnose), 6-deoxy-L-galactose (L-fucose), 6-deoxy-D-glucose (quinovose), and their derivatives, occur very widely in natural products. Also relevant are dideoxy and trideoxy sugars, such as 3,6-dideoxyhexoses, antigenic determinants of the lipopolysaccharides of bacteria, and the 2,6-dideoxy hexoses present in many steroidal glycosides, antibiotics, and antitumor compounds. In part, the role that they play in many physiological processes is attributed to the enhanced hydrophobicity that they show with respect to the oxygenated analogues. A previous survey on these compounds, by Hanessian, appeared in Vol. 21 of this Series. Chemical and biochemical aspects of deoxy sugars and deoxy sugar oligosaccharides have been reviewed. The synthesis of 2-deoxyglycosides has been reviewed for the period 1988-1999. Methods for the total synthesis of deoxy sugars starting from non-carbohydrate precursors has been recently compiled, and only a few examples will be given in this chapter. The naturally occurring 6-deoxyhexoses were reviewed previously in this Series.             Deoxy derivatives have been prepared for studies on the specificity or as inhibitors of glycosidases, or glycosyltransferases , and also to establish which hydroxyl groups are involved in the interaction with lectins.