Carbasugar Probes to Explore the Enzyme Binding Pocket at the Anomeric Position: Application to the Design of Golgi Mannosidase II Inhibitors

A methodology is described for the highly efficient and divergent synthesis of pseudosugars which allows the stereoselective introduction of polar groups at either the α or the β pseudoanomeric positions. Using this method, a series of 3-deoxycarbasugar analogues of mannose bearing a pyridyl group are rationally designed, prepared and tested for inhibition of Golgi α-mannosidase II.