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Reactive Sulfur Species: Kinetics and Mechanisms of the Oxidation of Cysteine by Hypohalous Acid to Give Cysteine Sulfenic Acid
Abstract
Cysteine sulfenic acid has been generated in alkaline aqueous solution by oxidation of cysteine with hypohalous acid (HOX, X = Cl or Br). The kinetics and mechanisms of the oxidation reaction and the subsequent reactions of cysteine sulfenic acid have been studied by stopped-flow spectrophotometry between pH 10 and 14. Two reaction pathways were observed: (1) below pH 12, the condensation of two sulfenic acids to give cysteine thiosulfinate ester followed by the nucleophilic attack of cysteinate on cysteine thiosulfinate ester and (2) above pH 10, a pH-dependent fast equilibrium protonation of cysteine sulfenate that is followed by rate-limiting comproportionation of cysteine sulfenic acid with cysteinate to give cystine. The observation of the first reaction suggests that the condensation of cysteine sulfenic acid to give cysteine thiosulfinate ester can be competitive with the reaction of cysteine sulfenic acid with cysteine.
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Pattison, D. I., Hawkins, C. L., & Davies, M. J. (2003) · Chemical Research in Toxicology · doi:10.1021/tx025670s · Cited by 139
Cited by
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Winterbourn, C. C., & Hampton, M. B. (2008) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2008.05.004 · Cited by 1,226
Nagy, P. (2013) · Antioxidants & Redox Signaling · doi:10.1089/ars.2012.4973 · Cited by 477
Self-citationProtein sulfenic acid formation: From cellular damage to redox regulation
Roos, G., & Messens, J. (2011) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2011.04.031 · Cited by 273
Storkey, C., Davies, M. J., & Pattison, D. I. (2014) · Free Radical Biology and Medicine · doi:10.1016/j.freeradbiomed.2014.04.024 · Cited by 165
One- and two-electron oxidation of thiols: mechanisms, kinetics and biological fates
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Metadata
- Authors
- Nagy, P., & Ashby, M. T.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2007-10-16
- Volume
- 129
- Issue
- 45
- Pages
- 14082-14091
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2026289840
- Cited by
- 178
- References
- 1
- FWCI
- 4.65
- Type
- journal article
- Language
- en
- Open access
- closed
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