Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Comparative Study
. 2016 May 18;27(5):1411-8.
doi: 10.1021/acs.bioconjchem.6b00181. Epub 2016 May 9.

Reactivity, Selectivity, and Stability in Sulfenic Acid Detection: A Comparative Study of Nucleophilic and Electrophilic Probes

Vinayak Gupta  1 , Hanumantharao Paritala  1 , Kate S Carroll  1
Affiliations
Comparative Study

Reactivity, Selectivity, and Stability in Sulfenic Acid Detection: A Comparative Study of Nucleophilic and Electrophilic Probes

Vinayak Gupta et al. Bioconjug Chem. .

Abstract

The comparative reaction efficiencies of currently used nucleophilic and electrophilic probes toward cysteine sulfenic acid have been thoroughly evaluated in two different settings-(i) a small molecule dipeptide based model and (ii) a recombinant protein model. We further evaluated the stability of corresponding thioether and sulfoxide adducts under reducing conditions which are commonly encountered during proteomic protocols and in cell analysis. Powered by the development of new cyclic and linear C-nucleophiles, the unsurpassed efficiency in the capture of sulfenic acid under competitive conditions is achieved and thus holds great promise as highly potent tools for activity-based sulfenome profiling.

PubMed Disclaimer

Figures

Fig. 1
Fig. 1
Dual chemical reactivity of sulfenic acid.
Fig. 2
Fig. 2
Nucleophilic and electrophilic probes reported for detecting sulfenic acid.
Fig. 3
Fig. 3
Nucleophiles and electrophiles tested for reactivity with sulfenic acid 10.
Fig. 4
Fig. 4
Reactivity of nucleophiles and electrophiles with Gpx3-SOH.
Fig. 5
Fig. 5
Effect of C-2 substitution on the UV-vis and fluorescence properties of the nucleophiles and corresponding thioether adducts.
Fig. 6
Fig. 6
Ratification of various nucleophiles and electrophiles on the basis of sulfenic acid reactivity and stability/reversibility of corresponding thioether (or sulfoxide) adduct.
See this image and copyright information in PMC

References

    1. Reddie KG, Carroll KS. Expanding the functional diversity of proteins through cysteine oxidation. Curr Opin Chem Biol. 2008;12:746–754. - PubMed
    1. Paulsen CE, Carroll KS. Orchestrating redox signaling networks through regulatory cysteine switches. ACS Chem Biol. 2010;5:47–62. - PMC - PubMed
    1. Lo Conte M, Carroll KS. The redox biochemistry of protein sulfenylation and sulfinylation. J Biol Chem. 2013;288:26480–26488. - PMC - PubMed
    1. Paulsen CE, Carroll KS. Cysteine-mediated redox signaling: chemistry, biology, and tools for discovery. Chem Rev. 2013;113:4633–4679. - PMC - PubMed
    1. Gupta V, Carroll KS. Sulfenic acid chemistry, detection and cellular lifetime. Biochim Biophys Acta. 2014;1840:847–875. - PMC - PubMed

Publication types