Evaluating N-benzylgalactonoamidines as putative transition state analogs for β-galactoside hydrolysis
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.
Fan, Q., Striegler, S., Langston, R. G., & Barnett, J. D. (2014). Evaluating N-benzylgalactonoamidines as putative transition state analogs for β-galactoside hydrolysis. Organic & Biomolecular Chemistry, 12(17), 2792-2800. doi:10.1039/C4OB00153B