Abstract
The potency of 2-deoxy-2-fluoroglycosides in activity-based profiling of human acid β-glucosidase is drastically improved by introducing an N-phenyl trifluoroacetimidate leaving group at the anomeric center. Protonation by the general acid-base catalyst in the active site turned out to be a prerequisite, making the imidate probe a genuine mechanism-based glycosidase inactivator.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetamides / chemistry*
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Acetamides / metabolism
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Fluoroacetates / chemistry*
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Fluoroacetates / metabolism
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Glycosides / chemistry*
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Glycosides / metabolism
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Humans
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Molecular Probes / chemistry
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Molecular Probes / metabolism*
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Molecular Structure
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beta-Glucosidase / analysis*
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beta-Glucosidase / antagonists & inhibitors
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beta-Glucosidase / metabolism*
Substances
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Acetamides
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Fluoroacetates
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Glycosides
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Molecular Probes
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beta-Glucosidase