Chemical Modification of the β-Glucocerebrosidase Inhibitor N-Octyl-β-valienamine: Synthesis and Biological Evaluation of 4-Epimeric and 4-O-(β-d-Galactopyranosyl) Derivatives Original Research Article

N-Octyl-β-valienemine (1), a potent β-glucocerebrosidase inhibitor, was chemically transformed into two biologically interesting compounds: the 4-epimer , β-galacto-type N-octyl-valienamine, and the 4-O-(β-d-galactopyranosyl) derivative , a carba-lactosylceramide analogue. The former, interestingly, could be demonstrated to act as a very effective inhibitor (IC50=0.3 μM) of human β-galactosidase. The latter exhibited moderate inhibitory activity (IC50=20 μM) against β-glucocerebrosidase (mouse liver).