Synthesis and evaluation of sulfonium analogues of isofucofagomine as glycosidase inhibitors

Abstract

A series of L-fucopyranose analogues having a sulfur substituent at the anomeric position were synthesised. A sulfide, a methylsulfonium ion, a sulfoxide and a sulfone analogue were made. The synthesised compounds were tested for inhibition of two α-fucosidases. The methylsulfonium ion was found to be a moderately strong competitive inhibitor, and 700 times more potent than the corresponding sulfide.