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Requirements for superoxide-dependent tyrosine hydroperoxide formation in peptides
Open accessAbstract
Superoxide reacts rapidly with other radicals, but these reactions have received little attention in the context of oxidative stress. For tyrosyl radicals, reaction with superoxide is 3-fold faster than dimerization, and forms the addition product tyrosine hydroperoxide. We have explored structural requirements for hydroperoxide formation using tyrosine analogues and di- and tri-peptides. Superoxide and phenoxyl radicals were generated using xanthine oxidase, peroxidase and the respective tyrosine derivative, or by γ-radiation. Peroxides were measured using FeSO4/Xylenol Orange. Tyrosine and tyramine formed stable hydroperoxides, but N-acetyltyrosine and p-hydroxyphenylacetic acid did not, demonstrating a requirement for a free amino group. Using [14C]tyrosine, the hydroperoxide and dityrosine were formed at a molar ratio of 1.8:1. Studies with pre-formed hydroperoxides, and measurements of substrate losses, indicated that, in the absence of a free amino group, reaction with superoxide resulted primarily in restitution of the parent compound. With dipeptides, hydroperoxides were formed only on N-terminal tyrosines. However, adjacent lysines promoted hydroperoxide formation, as did addition of free lysine or ethanolamine. Results are compatible with a mechanism [d'Alessandro, Bianchi, Fang, Jin, Schuchmann and von Sonntag (2000) J. Chem. Soc. Perkin Trans. II, 1862–1867] in which the phenoxyl radicals react initially with superoxide by addition, and the intermediate formed either releases oxygen to regenerate the parent compound or is converted into a hydroperoxide. Amino groups favour hydroperoxide formation through Michael addition to the tyrosyl ring. These studies indicate that tyrosyl hydroperoxides should be formed in proteins where there is a basic molecular environment. The contribution of these radical reactions to oxidative stress warrants further investigation.
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“For tyrosyl radicals, the reaction with superoxide to form the addition product (tyrosine hydroperoxide) is three times faster than dimerization [139,141].”
From Superoxide Anion Chemistry—Its Role at the Core of the Innate Immunity (2023) · cites this paper as [139]
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“The hydroperoxide, due to the resonant forms of Tyr, can be formed in the ortho or para position with respect to the phenoxyl radical [138,139,140], Figure 51 and Figure 52.”
From Superoxide Anion Chemistry—Its Role at the Core of the Innate Immunity (2023) · cites this paper as [139]
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Metadata
- Authors
- WINTERBOURN, C. C., PARSONS-MAIR, H. N., GEBICKI, S., GEBICKI, J. M., & DAVIES, M. J.
- Affiliations
- Department of Pathology, Christchurch School of Medicine and Health Sciences, P.O. Box 4345, Christchurch, New Zealand
- Macquarie University (AU)
- The Heart Research Institute (AU)
- Venue
- Biochemical Journal
- Publisher
- Portland Press Ltd.
- Published
- 2004-06-22
- Volume
- 381
- Issue
- 1
- Pages
- 241-248
- ISSN
- 0264-6021 (ISSN-L)
- 1470-8728
- PMC
- PMC1133782
- OpenAlex
- W1970577924
- Cited by
- 112
- References
- 48
- Citations by year
- 2026: 2 · 2025: 5 · 2024: 3 · 2023: 6 · 2022: 5 · 2021: 4 · 2020: 5 · 2019: 7 · 2018: 9 · 2017: 3 · 2016: 5 · 2015: 6 · 2014: 6 · 2013: 4 · 2012: 7
- FWCI
- 1.54
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- Biochemical Journal (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Research at the University of Copenhagen (University of Copenhagen) (submittedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Health Sciences › Medicine › Biochemistry (medical) › Antioxidant Activity and Oxidative Stress
- Keywords
- superoxide, tyrosyl radical, phenoxyl radicals, oxidative stress, tyrosine analogues, dipeptides, tripeptides, free amino groups, Michael addition, dityrosine, lysine, tyramine, N-acetyltyrosine, p-hydroxyphenylacetic acid, radical addition, protein oxidation
- MeSH terms
- Amines, Free Radicals, Hydrogen Peroxide, Models, Chemical, Peptides, Superoxides, Tyrosine, Dimerization
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