Cys-sulfenyl chloride is converted to Cys-sulfenic acid

Stable Identifier
Reaction [transition]
Homo sapiens
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Thiol-containing cysteine (Cys) residues are reactive with species of the oxidative burst. Hypochlorous acid (HOCl) leads to chlorination of Cys residues forming Cys-sulfenic acid (Cys-SOH) intermediates, which can either form a disulfide with an adjacent thiol or be further oxidized by HOCl to generate Cys- sulfinic and Cys-sulfonic acids sequentially (Peskin AV & Winterbourn CC 2001; Hawkins CL et al. 2003; Paulsen CE & Carroll KS 2013; Winterbourn CC & Kettle AJ 2013). Disulfides function as redox switches to control protein activity and protect thiol groups against overoxidation to Cys-sulfinic and -sulfonic acids (Paulsen CE & Carroll KS 2013).

Literature References
PubMed ID Title Journal Year
14661089 Hypochlorite-induced oxidation of amino acids, peptides and proteins

Davies, MJ, Pattison, DI, Hawkins, CL

Amino Acids 2003
11182528 Kinetics of the reactions of hypochlorous acid and amino acid chloramines with thiols, methionine, and ascorbate

Peskin, AV, Winterbourn, CC

Free Radic. Biol. Med. 2001
23514336 Cysteine-mediated redox signaling: chemistry, biology, and tools for discovery

Carroll, KS, Paulsen, CE

Chem. Rev. 2013
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