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Issue 17, 2014
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Evaluating N-benzylgalactonoamidines as putative transition state analogs for β-galactoside hydrolysis

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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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Publication details

The article was received on 21 Jan 2014, accepted on 07 Mar 2014 and first published on 26 Mar 2014


Article type: Paper
DOI: 10.1039/C4OB00153B
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 2792-2800
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    Evaluating N-benzylgalactonoamidines as putative transition state analogs for β-galactoside hydrolysis

    Q. Fan, S. Striegler, R. G. Langston and J. D. Barnett, Org. Biomol. Chem., 2014, 12, 2792
    DOI: 10.1039/C4OB00153B

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