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Abstract

Activated fluorosugars are covalent inactivators for a number of glycosidases, functioning through accumulation of stable glycosyl-enzyme intermediates. Two approaches were taken in designing new inactivators: more highly fluorinated sugars that could form more stable intermediates, and fluorosugars bearing novel aglycones that could be manipulated to improve selectivity and efficiency. Six novel difluorosugar fluorides were synthesized and evaluated as covalent inactivators. Four of the compounds were tested as time-dependent inactivators of the β-glucosidase from Agrobacterium sp. (Abg) and, while they were shown to behave as reversible competitive inhibitors, the only time-dependent inactivation was traced to the presence of an extremely small amount (