N-Benzylgalactonoamidines as potent β-galactosidase inhibitors

Authors

Rami Kanso, University of Arkansas, Fayetteville
Elizabeth Yancey, University of Arkansas, Fayetteville
Susanne Striegler, University of Arkansas, FayettevilleFollow

Document Type

Article - Abstract Only

Publication Date

2011

Keywords

Inhibitor, Amidine, β-galactosidase

Abstract

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.

Comments

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.

Citation

Kanso, R., Yancey, E., & Striegler, S. (2011). N-Benzylgalactonoamidines as potent β-galactosidase inhibitors. Tetrahedron, 68 (1), 47-52. https://doi.org/10.1016/j.tet.2011.10.048