Synthesis and glycosidase inhibitory activity of some N-substituted 5a-carba-β-fuco- and β-galactopyranosylamines, and selected derivatives Original Research Article

In the course of chemical modification of α-fucosidase inhibitors of 5a-carba-fucopyranosylamine type, an N-dodecyl derivative of the enantiomer 6-deoxy-5a-carba-β-d-galactopyranosylamine demonstrated very strong inhibition of β-galactosidase and β-glucosidase. This finding led us to synthesize corresponding 6-hydroxy compounds, in order to elucidate structure–activity relationships for inhibitors of this type. Among four N-alkyl-5a-carba-β-d-galactopyranosylamines prepared, the N-octyl derivative could be demonstrated to possess moderate activity toward α- and β-galactosidases, and β-glucosidase.