| The control of glycosidase enzyme inhibition is of great importance in processing carbohydrate containing biopolymers such as glycoproteins and glycolipids. These biopolymers are coated on the surfaces of cells and as such mediate cell-cell and cell-virus interactions. It is hoped that disrupting the enzymes responsible for their biosynthesis may alter these interactions.; The low affinity of carbohydrate-protein interactions has led to the evolution of non-carbohydrate mimics as natural inhibitors for these enzymes. Recently, the glucosidase inhibitors salacinol and kotalanol were isolated from Salacia reticulata, a plant known for its anti-diabetic properties. These molecules constitute a new class of glycosidase inhibitors in that they contain a unique thiosugar sulfonium ion with an internal sulfate providing the counterion. Hence, we designed six-membered heterocyclic ring analogues of salacinol as potential therapeutic agents, with the expectation that these molecules will mimic the shape and/or charge of the putative transition state in a glycosidase-mediated hydrolysis reaction. (Abstract shortened by UMI.)... |
