Transnitrosation between nitrosothiols and thiols
Abstract
Transfer of the nitroso group from nitrosothiols to thiols occurs very readily in aqueous solution particularly at pH > ≈8. The results are consistent with attack by the thiolate anion at the nitroso nitrogen atom of the nitrosothiol. Results have been obtained for the reaction of S-nitroso-N-acetylpenicillamine (SNAP) with thioglycolic acid and also for the reaction of S-nitrosocysteine (SNCys) with thiomalic acid. Both reactions showed the same kinetic characteristics. The results are discussed in terms of transnitrosation reactions of nitroso compounds generally, and also in the case of nitrosothiols, in terms of possible in vivo transnitrosation and subsequent decomposition of a possibly more unstable nitrosothiol to yield nitric oxide; this may have implications for the mechanism of action of nitric oxide in a range of physiological processes.
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A central signaling reaction of S-nitrosothiols is their ability to act as nitrosating agents through transnitrosation.
“Perhaps the central reaction in terms of signaling is the ability to serve as a nitrosating agent through transnitrosation (Eq. 16) [174].”
From Signaling and stress: The redox landscape in NOS2 biology (2015) · cites this paper as [174]
Nitrosation favors thiols with a lower pKa.
“Their data showed that the nitrosation favored thiols with a lower pKa.”
From On the chemical biology of the nitrite/sulfide interaction (2015) · cites this paper as [96]
The reaction of transnitrosation between nitrosothiols and thiols is very fast, requiring stopped-flow techniques for kinetics.
“They found the reaction to be very fast, requiring stopped-flow techniques for investigating the kinetics.”
From On the chemical biology of the nitrite/sulfide interaction (2015) · cites this paper as [96]
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- Authors
- Barnett, D. J., McAninly, J., & Williams, D. L. H.
- Venue
- Journal of the Chemical Society Perkin Transactions 2
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 1994
- Issue
- 6
- Pages
- 1131
- ISSN
- 0300-9580 (ISSN-L)
- 1364-5471
- OpenAlex
- W2029842625
- Cited by
- 75
- References
- 9
- Citations by year
- 2026: 1 · 2022: 1 · 2020: 1 · 2016: 4 · 2015: 1 · 2014: 3 · 2013: 1
- FWCI
- 4.01
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the Chemical Society Perkin Transactions 2 (publishedVersion)
- Funders
- Wellcome Trust
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Health Sciences › Medicine › Physiology › Nitric Oxide and Endothelin Effects
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Keywords
- transnitrosation, S-nitrosothiols, thiols, S-nitroso-N-acetylpenicillamine, S-nitrosocysteine, thioglycolic acid, thiomalic acid, reaction kinetics, nitric oxide
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