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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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
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author Weber, Patrick
Fischer, Roland
Nasseri, Seyed A.
Stütz, Arnold E.
Thonhofer, Martin
Withers, Stephen G.
Wolfsgruber, Andreas
Wrodnigg, Tanja M.
author_facet Weber, Patrick
Fischer, Roland
Nasseri, Seyed A.
Stütz, Arnold E.
Thonhofer, Martin
Withers, Stephen G.
Wolfsgruber, Andreas
Wrodnigg, Tanja M.
author_sort Weber, Patrick
collection PubMed
description 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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spelling pubmed-90299922022-04-26 New α-galactosidase-inhibiting aminohydroxycyclopentanes Weber, Patrick Fischer, Roland Nasseri, Seyed A. Stütz, Arnold E. Thonhofer, Martin Withers, Stephen G. Wolfsgruber, Andreas Wrodnigg, Tanja M. RSC Adv Chemistry 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. The Royal Society of Chemistry 2021-04-29 /pmc/articles/PMC9029992/ /pubmed/35481199 http://dx.doi.org/10.1039/d1ra02507d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Weber, Patrick
Fischer, Roland
Nasseri, Seyed A.
Stütz, Arnold E.
Thonhofer, Martin
Withers, Stephen G.
Wolfsgruber, Andreas
Wrodnigg, Tanja M.
New α-galactosidase-inhibiting aminohydroxycyclopentanes
title New α-galactosidase-inhibiting aminohydroxycyclopentanes
title_full New α-galactosidase-inhibiting aminohydroxycyclopentanes
title_fullStr New α-galactosidase-inhibiting aminohydroxycyclopentanes
title_full_unstemmed New α-galactosidase-inhibiting aminohydroxycyclopentanes
title_short New α-galactosidase-inhibiting aminohydroxycyclopentanes
title_sort new α-galactosidase-inhibiting aminohydroxycyclopentanes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9029992/
https://www.ncbi.nlm.nih.gov/pubmed/35481199
http://dx.doi.org/10.1039/d1ra02507d
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