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Issue 6, 2008
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A chemical approach for detecting sulfenic acid-modified proteins in living cells

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Abstract

Oxidation of the thiol functional group in cysteine (Cys–SH) to sulfenic (Cys–SOH), sulfinic (Cys–SO2H) and sulfonic acids (Cys–SO3H) is emerging as an important post-translational modification that can activate or deactivate the function of many proteins. Changes in thiol oxidation state have been implicated in a wide variety of cellular processes and correlate with disease states but are difficult to monitor in a physiological setting because of a lack of experimental tools. Here, we describe a method that enables live cell labeling of sulfenic acid-modified proteins. For this approach, we have synthesized the probe DAz-1, which is chemically selective for sulfenic acids and cell permeable. In addition, DAz-1 contains an azide chemical handle that can be selectively detected with phosphine reagents via the Staudinger ligation for identification, enrichment and visualization of modified proteins. Through a combination of biochemical, mass spectrometry and immunoblot approaches we characterize the reactivity of DAz-1 and highlight its utility for detecting proteinsulfenic acids directly in mammalian cells. This novel method to isolate and identify sulfenic acid-modified proteins should be of widespread utility for elucidating signaling pathways and regulatory mechanisms that involve oxidation of cysteineresidues.

Graphical abstract: A chemical approach for detecting sulfenic acid-modified proteins in living cells

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Publication details

The article was received on 03 Jan 2008, accepted on 06 Feb 2008 and first published on 14 Mar 2008


Article type: Paper
DOI: 10.1039/B719986D
Mol. BioSyst., 2008,4, 521-531

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    A chemical approach for detecting sulfenic acid-modified proteins in living cells

    K. G. Reddie, Y. H. Seo, W. B. Muse III, S. E. Leonard and K. S. Carroll, Mol. BioSyst., 2008, 4, 521
    DOI: 10.1039/B719986D

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