Novel easily accessible glucosidase inhibitors: 4-hydroxy-5-alkoxy-1,2-cyclohexanedicarboxylic acids

Glycosidases are very important enzymes involved in a variety of biochemical processes with a special importance to biotechnology, food industry, and pharmacology. Novel structurally simple inhibitors derived from cyclohexane-1,2-dicarboxylic acids were synthesized and tested against several fungal glycosidases from Aspergillus oryzae and Penicillium canescens. The presence of at least two carboxylic groups and one hydroxy group was essential for efficient inhibition. Significant selective inhibition was observed for alpha- and beta-glucosidases, the magnitude of which depended on the configuration of substituents; inhibition increased for p-glucosidase by lengthening the alkoxy group of the inhibitor. (C) 2008 Elsevier Ltd. All rights reserved.