Issue 5, 2015

Sulfonyl fluorides as privileged warheads in chemical biology


Sulfonyl fluoride electrophiles have found significant utility as reactive probes in chemical biology and molecular pharmacology. As warheads they possess the right balance of biocompatibility (including aqueous stability) and protein reactivity. Their functionality is privileged in this regard as they are known to modify not only reactive serines (resulting in their common use as protease inhibitors), but also context-specific threonine, lysine, tyrosine, cysteine and histidine residues. This review describes the application of sulfonyl fluoride probes across various areas of research and explores new approaches that could further enhance the chemical biology toolkit. We believe that sulfonyl fluoride probes will find greater utility in areas such as covalent enzyme inhibition, target identification and validation, and the mapping of enzyme binding sites, substrates and protein–protein interactions.

Graphical abstract: Sulfonyl fluorides as privileged warheads in chemical biology

Article information

Article type
03 Feb 2015
16 Mar 2015
First published
16 Mar 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2015,6, 2650-2659

Author version available

Sulfonyl fluorides as privileged warheads in chemical biology

A. Narayanan and L. H. Jones, Chem. Sci., 2015, 6, 2650 DOI: 10.1039/C5SC00408J

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