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Evaluating N-benzylgalactonoamidines as putative transition state analogs for ?-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-?-D-galactopyranosides by ?-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-?-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

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

Fan Qiu-Hua QH   Striegler Susanne S   Langston Rebekah G RG   Barnett James D JD  

Organic & biomolecular chemistry 20140501 17

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.  ...[more]

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