Synthesis fromD-glucose of 1,5-dideoxy-1,5-imino-L-fucitol, a potent α-L-fucosidase inhibitor

Abstract

1,5-Dideoxy-1,5-imino-L-fucitol (1), synthesised from methyl α-D-glucopyranoside, is a potent competitive inhibitor of the hydrolysis of p-nitrophenyl α-L-fucopyranoside catalysed by α-L-fucosidase (ex. bovine epididymis) causing 50% inhibition of enzymic activity at 2.5 × 10^–8 _M.