Novel O-glycosyl amino acid mimetics as building blocks for O-glycopeptides act as inhibitors of galactosidases

As potential lead structures for a new class of glycosidase inhibitors the novel O-glycosyl amino acid mimetics 3′-O-[2,6-anhydro- -glycero- -gluco-heptitol-1-yl]- -serine 3 and- -threonine 4 were synthesized, employing regio- and stereoselective aziridine ring opening methodology. They proved to be stable in the presence of glycosidases and showed competitive inhibition of α-galactosidase from Aspergillus niger.