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

Organic & Biomolecular Chemistry Pub Date: 2014-03-26 DOI: 10.1039/C4OB00153B

Abstract

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.

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