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Chem Commun (Camb). 2017 Jun 29;53(53):7385-7388. doi: 10.1039/c7cc02285a.

Chemoselective ratiometric imaging of protein S-sulfenylation.

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1
Department of Chemistry and Program in Chemical Biology, University of Michigan, 930 N. University Ave., Ann Arbor, MI, USA. brentrm@umich.edu.

Abstract

Here we report a ratiometric fluorescent probe for chemoselective conjugation to sulfenic acids in living cells. Our approach couples an α-fluoro-substituted dimedone to an aminonaphthalene fluorophore (F-DiNap), which upon sulfenic acid conjugation is locked as the 1,3-diketone, changing the fluorophore excitation. F-DiNap reacts with S-sulfenylated proteins at equivalent rates to current probes, but the α-fluorine substitution blocks side-reactions with biological aldehydes.

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