Chemoenzymatic Preparation of Novel Cyclic Imine Sugars and Rapid Biological Activity Evaluation Using Electrospray Mass Spectrometry and Kinetic Analysis

摘要

Cyclic imine sugars were prepared by a novel chemoenzymatic strategy in which azido-sugars, constructed by enzymatic aldol reactions, were hydrogenated under acidic conditions. These cyclic imine sugars were found to be potent inhibitors of glycoprocessing enzymes having K_I's in the nanomolar and micromolar range for a variety of glycosidases. In comparison with their fully hydrogenated counterparts the cyclic imine sugars generally showed comparable or better inhibition against the glycosidases tested.