Synthesis of Unsaturated Aminopyranosides as Possible Transition State Mimics for Glycosidases

Four unsaturated aminopyranosides have been prepared as possible transition‐state mimics targeted towards carbohydrate processing enzymes. The conformations of the protonated aminosugars have been investigated by molecular modelling and their ability to inhibit α‐ and β‐glucosidases and an α‐mannosidase have been probed. Two targets proved moderate inhibitors of α‐glucosidases from Brewer's yeast and Bacillus stearothermophilus.