Tuning the leaving group in 2-deoxy-2-fluoroglucoside results in improved activity-based retaining β-glucosidase probes.

doi:10.1039/C2CC35653H

Paper

Tuning the leaving group in 2-deoxy-2-fluoroglucoside results in improved activity-based retaining β-glucosidase probes.

Published Sep 26, 2012 · M. Walvoort, W. Kallemeijn, Lianne I. Willems

Chemical communications

Q1 SJR score

25

Citations

2

Influential Citations

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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.

Study Snapshot

The improved 2-deoxy-2-fluoroglycoside probes significantly enhance activity-based profiling of human acid -glucosidase, making them a genuine mechanism-based glycosidase inactivator.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Tuning the leaving group in 2-deoxy-2-fluoroglucoside results in improved activity-based retaining β-glucosidase probes.

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References

Novel activity-based probes for broad-spectrum profiling of retaining β-exoglucosidases in situ and in vivo.

Cyclophellitol aziridine-type activity-based probes enable ultra-sensitive visualization of mammalian and non-mammalian -glucosidases, offering new ways to study these enzymes.

Conformational analyses of the reaction coordinate of glycosidases.

This study provides three-dimensional insights into the conformational changes directed by glycosidases, aiding in the design of enzyme inhibitors and understanding their role in diverse biological processes.

Tailoring the specificity and reactivity of a mechanism-based inactivator of glucocerebrosidase for potential therapeutic applications.

This study developed a new class of fluorosugar glycosidase inactivators with tunable phosphorus-based leaving groups that react with GCase over 4000 times faster than 2FGlcF, potentially offering a faster and more effective treatment for Gaucher's disease.

Irreversible inhibitors and activity-based probes as research tools in chemical glycobiology.

Irreversible inhibitors and activity-based probes are effective tools in studying enzymes involved in glycoconjugate synthesis and degradation, aiding in understanding alternative pathways for degradation.

Activity‐Based Profiling of Retaining β‐Glucosidases: A Comparative Study

Cyclic titol epoxides are the most effective activity-based probes for retaining -glucosidase activity, with direct labeling being more efficient and two-step bio-orthogonal labeling being effective for isolated enzymes.

Citations