Diastereoselective resolution of 6-substituted glycosides via enzymatic hydrolysis

Article abstract of DOI:10.1016/S0008-6215(97)00246-2

The diastereoselectivity of the enzymatic hydrolyses of 4-nitrophenyl 6- deoxy-6-methyl(R)- and (S)-sulfinyl-β-D-galactopyranoside (1a,b), 4- nitrophenyl 7-deoxy-D- and L-glycero-β-D-galacto-heptopyranoside (2a,b) and 4-nitrophenyl 6,7-anhydro-D- and L-glycero-β-Dgalacto-heptopyranoside (3a,b) was investigated using a range of crude glycosidase preparations. It was shown that the enzymes display a high degree of discrimination between diastereomers thereby demonstrating the utility of glycosidases for the diastereomeric resolution of unnatural 6-substituted monosaccharide derivatives.