The synthesis of diastereomeric epoxy(6-D-glucopyranosyl)ethanes and 1,2-epoxy-3-(β-D-glucopyranosyl)propanes, as irreversible inhibitors of β-D-glucosidase

Abstract Diastereomeric epoxy-(β- D -glucopyranosyl)ethanes and 1,2-epoxy-3-(β- D -glucopyranosyl)propanes were synthesized to study the active site of β- D -glucosidases. The mixtures of the diastereomeric epoxides of β- D -glucopyranosylethene and of 2-(β- D -glucopyranosyl)-1-propene tetraacetates were prepared by reaction of 2,3,4,6-tetra- O -acetyl-α- D -glucopyranosyl bromide with the appropriate Grignard reagents, followed by oxidation with peroxyphthalic acid in dichloromethane. Chromatographic separation of these mixtures, followed by deacetylation of each epoxide resulted in two pairs of diastereomers that inactivated irreversibly sweet-almond β- D -glucosidase.