Evaluating N-benzylgalactonoamidines as putative transition state analogs for beta-galactoside hydrolysis
by Fan, Qiu-Hua; Striegler, Susanne; Langston, Rebekah G.; Barnett, James D.
Experimental evidence is provided for p-methylbenzyl-D-galactonoamidine to function as a true transition state analog for the enzymatic hydrolysis of aryl-beta-D-galactopyranosides by beta-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-beta-D-galactopyranosides. Last, the stability of the galactonoamidines under the assay conditions was confirmed.
- Organic and Biomolecular Chemistry
- Start Page
- 1477-0539; 1477-0520