New α-galactosidase-inhibiting aminohydroxycyclopentanes

Patrick Weber*, Roland Fischer, Seyed A. Nasseri, Arnold Stütz, Martin Simon Thonhofer, Stephen G Withers, Andreas Wolfsgruber, Tanja Maria Wrodnigg

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


A set of cyclopentanoid α-galactosidase ligands was prepared from a partially protected ω-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 α-galactosidase inhibitors. Their glycosidase inhibitory activities were screened with a panel of standard glycosidases of biological significance.
Original languageEnglish
Pages (from-to)15943-15951
Number of pages9
JournalRSC Advances
Issue number26
Publication statusPublished - 22 Apr 2021

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)


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