Synthesis of novel glycoconjugates and evaluation as inhibitors against β-glucosidase from almond

Hydrolytic activity of glycosidases can be influenced by inhibitors of glycosidic nature. We have synthetized a serie of glycoconjugates consisting of galactose, glucosaminide or lactose 1-O-linked with allyl alcohol, pentenol or tetraethyleneglycol moieties. These compounds were found to be inhibitors of the hydrolase activity of the β-glucosidase from almond, with Ki in the range of 7.7–107 mM and presenting different types of inhibition. Based on the structure of the functionalized glycosides and the inhibition studies performed, we suggest that the nature of the carbohydrate is determinant in the inhibitory strength of these glycoconjugates.