Rational Tuning of Fluorobenzene Probes for Cysteine-Selective Protein Modification

Angewandte Chemie
Ahmed M EmbabyFrederik Diness

Abstract

Fluorobenzene probes for protein profiling through selective cysteine labeling have been developed by rational reactivity tuning. Tuning was achieved by selecting an electron-withdrawing para substituent in combination with variation of the number of fluorine substituents. Optimized probes chemoselectively arylated cysteine residues in proteins under aqueous conditions. Probes linked to azide, biotin, or a fluorophore were applicable to labeling of eGFP and albumin. Selective inhibition of cysteine proteases was also demonstrated with the probes. Additionally, probes were tuned for site-selective labeling of cysteine residues and for activity-based protein profiling in cell lysates.

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Citations

Nov 7, 2018·Angewandte Chemie·Chi ZhangBradley L Pentelute
Jan 4, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Arduino A MangoniDiego Muñoz-Torrero
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Jan 4, 2020·The Journal of Organic Chemistry·Zhanfeng HouZigang Li
Nov 12, 2021·Chemistry : a European Journal·William D G Brittain, Christopher R Coxon
Dec 14, 2021·Chemistry : a European Journal·Niklas Henrik FischerFrederik Diness

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