New Alpha-Galactosidase-Inhibiting Aminohydroxycyclopentanes

A set of cyclopentanoid alpha-galactosidase ligands was prepared from a partially protected omega-eno-aldose via a reliable (2 + 3)-cycloaddition protocol with slightly modified conditions. The obtained N-benzylisoxazolidine ring was selectively opened and the configuration of the hydroxymethylgroup was inverted. Consecutive deprotection provided an aminocyclopentane, which was N-alkylated to furnish a set of potential alpha-galactosidase inhibitors. Their glycosidase inhibitory activities were screened with a panel of standard glycosidases of biological significance.