A bioisosteric oligosaccharide mimetic based on isofagomine-type monomers

Abstract

A series of hydroxylated piperidine oligomers that resemble oligosaccharides is synthesised. Prepared were 5, a mimic of 3-O-L-fucopyranosyl-D-galactopyranose, 6, a mimic of 3-O-D-galactopyranosyl-D-galactopyranose and 7, a mimic of 3-O-{3-O-[3-O-(L-fucopyranosyl)-D-galactopyranosyl]-D-galactopyranosyl}-D-galactopyranose. Conformational analysis of the new compounds using NMR spectroscopy showed them to have predominant conformations that were similar to those adopted by β-O-glycosides. The inhibition of a series of glycosidases by 5–7 was investigated and found to be inferior to that of the corresponding unsubstituted isofagomines.