PMID:3286645
| Citation |
Withers, SG, Rupitz, K and Street, IP (1988) 2-Deoxy-2-fluoro-D-glycosyl fluorides. A new class of specific mechanism-based glycosidase inhibitors. J. Biol. Chem. 263:7929-32 |
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| Abstract |
Mechanism-based glycosidase inhibitors are of considerable use in studies of enzyme mechanism, in studies of glycoprotein processing, and possibly therapeutically in control of sugar uptake. This paper describes a new general approach to mechanism-based inactivation of glycosidases which involves trapping a covalent glycosyl enzyme intermediate. This is achieved by use of 2-deoxy-2-fluoro-D-glycosyl fluorides, for which the rate of hydrolysis of the fluoroglycosyl enzyme intermediate is extremely slow, resulting in accumulation of the intermediate. Eleven different glycosidases were tested with their corresponding 2-deoxy-2-fluoro-D-glycosyl fluorides. Eight of the eleven were inactivated, four of them according to pseudo first-order kinetics and four according to a more complex kinetic scheme. The specificity of these inhibitors was investigated by assaying for inhibition of one enzyme with four different 2-deoxy-2-fluoro-D-glycosyl fluorides. Large differences in inactivation rate were observed which paralleled previously observed substrate specificities. |
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| Keywords |
Alcaligenes/enzymology; Animals; Cattle; Escherichia coli/enzymology; Fluorine/pharmacology; Glycoside Hydrolases/antagonists & inhibitors; Glycosides/pharmacology; Models, Chemical; Plants/enzymology; Saccharomyces cerevisiae/enzymology |
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