Galacto configured N-aminoaziridines: a new type of irreversible inhibitor of β-galactosidases

A new type of galactose mimetics has been synthesized following a straightforward synthetic approach based on cyclohexene olefin aziridination reactions directed by hydroxyl substituents. These enantiomerically pure galacto-configured N-aminoaziridines are potent irreversible inhibitors of Aspergillus oryzae and Escherichia coli beta-galactosidases.