biostudies-literatureWeber PAustrian Science Fund FWF15943-15951https://www.ebi.ac.uk/biostudies/studies/S-EPMC9029992biostudies-literatureUnknown11(26)A set of cyclopentanoid α-galactosidase ligands was prepared from a partially protected ω-eno-aldose <i>via</i> a reliable (2 + 3)-cycloaddition protocol with slightly modified conditions. The obtained <i>N</i>-benzylisoxazolidine ring was selectively opened and the configuration of the hydroxymethylgroup was inverted. Consecutive deprotection provided an aminocyclopentane, which was <i>N</i>-alkylated to furnish a set of potential α-galactosidase inhibitors. Their glycosidase inhibitory activities were screened with a panel of standard glycosidases of biological significance.RSC advancesNew α-galactosidase-inhibiting aminohydroxycyclopentanes.PMC9029992P 30372Wolfsgruber AFischer RNasseri SAWithers SGThonhofer MStutz AEWeber PWrodnigg TMfalseNew α-galactosidase-inhibiting aminohydroxycyclopentanes.A set of cyclopentanoid α-galactosidase ligands was prepared from a partially protected ω-eno-aldose <i>via</i> a reliable (2 + 3)-cycloaddition protocol with slightly modified conditions. The obtained <i>N</i>-benzylisoxazolidine ring was selectively opened and the configuration of the hydroxymethylgroup was inverted. Consecutive deprotection provided an aminocyclopentane, which was <i>N</i>-alkylated to furnish a set of potential α-galactosidase inhibitors. Their glycosidase inhibitory activities were screened with a panel of standard glycosidases of biological significance.2021-01-01T00:00:00Z2021 Apr2025-04-05T11:05:16.717Z2025-04-05T11:05:16.717ZS-EPMC90299923548119910.1039/d1ra02507d