New α-galactosidase-inhibiting aminohydroxycyclopentanes

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 inv...

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Detalles Bibliográficos
Autores principales: Weber, Patrick, Fischer, Roland, Nasseri, Seyed A., Stütz, Arnold E., Thonhofer, Martin, Withers, Stephen G., Wolfsgruber, Andreas, Wrodnigg, Tanja M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9029992/
https://www.ncbi.nlm.nih.gov/pubmed/35481199
http://dx.doi.org/10.1039/d1ra02507d
Descripción
Sumario: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.

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