Evaluating N-benzylgalactonoamidines as putative transition state analogs for β-galactoside hydrolysis

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Article - Abstract Only

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Stability assays, kinetic assays, synthetic procedures


Experimental evidence is provided for p-methylbenzyl-D-galactonoamidine to function as a true transition state analog for the enzymatic hydrolysis of aryl-β-D-galactopyranosides by β-galactosidase (A. oryzae). The compound exhibits inhibition constants in the low nanomolar concentration range (12–56 nM) for a selection of substrates. Along these lines, a streamlined synthetic method based on phase-transfer catalysis was optimized to afford the required variety of new aryl-β-D-galactopyranosides. Last, the stability of the galactonoamidines under the assay conditions was confirmed.


An undergraduate research fellowship of the University of Arkansas Honors College to R.G.L. and support by the National Science Foundation (CHE-1244755, CHE-1305543) to S. S. are gratefully acknowledged. This study was furthermore supported by Grant Number P30 GM103450 from the National Institute of General Medical Sciences (NIGMS) of the National Institutes of Health (NIH).

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