Glycosidase Inhibition by All 10 Stereoisomeric 2,5-Dideoxy-2,5- iminohexitols Prepared from the Enantiomers of Glucuronolactone

摘要

The enantiomers of glucuronolactone arenexcellent chirons for the synthesis of the 10 stereoisomericn2,5-dideoxy-2,5-iminohexitols by formation of the pyrrolidinenring by nitrogen substitution at C2 and C5, with eithernretention or inversion of configuration; the stereochemistry atnC3 may be adjusted during the synthesis to give sevennstereoisomers from each enantiomer. A definitive side-by-sidencomparison of the glycosidase inhibition of a panel of 13nglycosidases showed that 8 of the 10 stereoisomers showednsignificant inhibition of at least one glycosidase.