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)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.