Sugar hydrazide imides: a new family of glycosidase inhibitorsElectronic supplementary information (ESI) available: Synthetic details for the preparation of compounds and their NMR spectra. See DOI: 10.1039/c7ob01673e

Sugar hydrazide imides: a new family of glycosidase inhibitorsElectronic supplementary information (ESI) available: Synthetic details for the preparation of compounds and their NMR spectra. See DOI: 10.1039/c7ob01673e

The preparation of a novel type of iminosugar including a hydrazide imide moiety is described. The sugar hydrazide imides (3 S ,4 S ,5 R ,6 R )-1-amino-3,4,5-trihydroxy-6-(hydroxymethyl)-2-iminopiperidine acetate and (3 S ,4 S ,5 R ,6 R )-3,4,5-trihydroxy-6-(hydroxymethyl)-2-imino-1-(methylamino)pip...

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Hauptverfasser: Lindbäck, Emil, Lopéz, Óscar, Tobiesen, Ådne, Fernández-Bolaños, José G, Sydnes, Magne O
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creator Lindbäck, Emil
Lopéz, Óscar
Tobiesen, Ådne
Fernández-Bolaños, José G
Sydnes, Magne O
description The preparation of a novel type of iminosugar including a hydrazide imide moiety is described. The sugar hydrazide imides (3 S ,4 S ,5 R ,6 R )-1-amino-3,4,5-trihydroxy-6-(hydroxymethyl)-2-iminopiperidine acetate and (3 S ,4 S ,5 R ,6 R )-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. We present a new type of glycosidase inhibitor including a unique hydrazide imide moiety, which displays inhibition in the low micromolar range.
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title Sugar hydrazide imides: a new family of glycosidase inhibitorsElectronic supplementary information (ESI) available: Synthetic details for the preparation of compounds and their NMR spectra. See DOI: 10.1039/c7ob01673e
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