The synthesis of new multivalent architectures based on a trihydroxypiperidine α-fucosidase inhibitor is reported herein. Tetravalent and nonavalent dendrimers were obtained by means of the click chemistry approach involving the copper azide-alkyne-catalyzed cycloaddition (CuAAC) between suitable scaffolds bearing terminal alkyne moieties and an azido-functionalized piperidine as the bioactive ...

A straightforward chiral pool synthesis for a non-natural calystegin, 3-epi-B2, is described. Key steps of this synthesis include an ultrasound-assisted Zn-mediated tandem ring opening reaction followed by a Grubbs’ catalyst-mediated ring closure metathesis reaction. Compared to calystegin B2, the target compound is no longer an inhibitor for a β -glycosidase hence proving that an equatorial hy...

Glycoside hydrolases are important enzymes in a number of essential biological processes. Irreversible inhibitors of this class of enzyme have attracted interest as probes of both structure and function. In this review we discuss some of the compounds used to covalently modify glycosidases, their use in residue identification, structural and mechanistic investigations, and finally their applica...

The synthesis of the enantiomers of 6-epicastanospermine and of 1,6-diepicastanospermine from the enantiomeric gulonolactones is reported and the structure of the former is established as (1S,6R,7R,8R,8aR)-1,6,7,8-tetrahydroxyoctahydroindolizine. The inhibitory activities of the diastereomers against the amyloglucosidase-catalysed hydrolysis of p-nitrophenyl alpha-D-glucopyranoside were investi...

Pronase digestion of the lima bean lectin (Phaseolus lunatus (alpha-D-GalNAc greater than alpha-D-Gal)) afforded a glycopeptide of molecular weight 1380. Amino acid and carbohydrate analysis showed the glycopeptide to contain fucose, mannose, glucosamine, and aspartic acid in the molar ratios, 0.8:4.4:1.9:1.0. Methylation analysis, Smith degradation, and sequential degradation by specific glyco...