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

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.

SUBMITTER: Fan QH 

PROVIDER: S-EPMC4096895 | biostudies-literature | 2014 May

REPOSITORIES: biostudies-literature