Lyann Sim

Graphical Abstract Cyclohexene-based carbohydrate mimics have been shown to react with glycoside hydrolases via positively charged, allylic cation-like transition states. By incorporating electron-withdrawing halogens at the vinyl position of the allyl ethers of these sugar mimics potent inhibitors of β-glycosidases were prepared. This approach is orthogonal to existing strategies and offers a new tool to probe glycosidase active sites.