The Interaction of Anhydroalditols with Sweet-Almond β-glucosidase and Escherichia coli β-galactosidase: implications for the design of potent glycosidase inhibitors

A range of 1,4- and 1,5-anhydroalditols have been synthesized and assessed for their ability to inhibit glycosidases. Observed inhibition indicates that aglycone-enzyme interactions contribute significantly to both the affinity and the stereoselectivity of substrate binding. Such interactions may also contribute to enzyme-transition state interactions. Implications for the design of potent glycosidase inhibitors are discussed.

A range of 1,5- and 1,4-anhydroalditols have been synthesized and assessed for their ability to act as substrate and transition-state analogue glycosidase inhibitors.