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 Penicilliumcanescens. The presence of at least two carboxylic groups and one hydroxy group was essential for efficient inhibition. Significant selective inhibition was observed for α- and β-glucosidases, the magnitude of which depended on the configuration of substituents; inhibition increased for β-glucosidase by lengthening the alkoxy group of the inhibitor.

Graphical abstractGlycosidases 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 toward several fungal glycosidases from Aspergillus oryzae and Penicilliumcanescens. The presence of at least two carboxylic groups and one hydroxy group was essential for efficient inhibition. Significant selective inhibition was observed for α- and β-glucosidases, which magnitude depended on configuration of substituents and increased for β-glucosidase with lengthening of the inhibitor’s alkoxy group.Figure optionsDownload full-size imageDownload as PowerPoint slide