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Sugar hydrazide imides: a new family of glycosidase inhibitors

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Abstract

The preparation of a novel type of iminosugar including a hydrazide imide moiety is described. The sugar hydrazide imides (3S,4S,5R,6R)-1-amino-3,4,5-trihydroxy-6-(hydroxymethyl)-2-iminopiperidine acetate and (3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-imino-1-(methylamino)piperidine acetate presented here behave as inhibitors of α/β-glucosidases in the low micromolar concentration range. The former inhibitor displays a pH-dependent inhibition of β-glucosidase. The N-methylated counterpart behaves as an anomer-selective competitive micromolar inhibitor of α-glucosidase.

Graphical abstract: Sugar hydrazide imides: a new family of glycosidase inhibitors

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Publication details

The article was received on 07 Jul 2017, accepted on 06 Oct 2017 and first published on 06 Oct 2017


Article type: Communication
DOI: 10.1039/C7OB01673E
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Sugar hydrazide imides: a new family of glycosidase inhibitors

    E. Lindbäck, Ó. Lopéz, Å. Tobiesen, J. G. Fernández-Bolaños and M. O. Sydnes, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01673E

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