N-Benzylgalactonoamidines as potent β-galactosidase inhibitors

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Article - Abstract Only

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Inhibitor, Amidine, β-galactosidase


A series of N-benzylgalactonoamidines was synthesized to probe their inhibitory ability during the hydrolysis of o-nitrophenyl-β-d-galactopyranoside by β-galactosidase (Aspergillus oryzae). All compounds are characterized as potent competitive inhibitors with inhibition constants (Ki) in the low nanomolar range (12–48 nM). The structure of the inhibitors mimics the bond-lengthening during the hydrolysis and the aromatic aglycon of the substrate. The electronic nature of the substituent in p-position of the aglycon influences the overall inhibitory ability most when compared to the unsubstituted parent compound.


A CAREER award from the National Science Foundation to S.S. (CHE-0746635) is gratefully acknowledged; the authors are also indebted to Christopher Easley and Joonyul Kim for conducting the gel electrophoresis experiments on the microchip.

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