The effect of oxygen, antioxidants, and superoxide radical on tyrosine phenoxyl radical dimerization
Abstract
Dimerization of tyrosine phenoxyl radical yields bityrosine (BT) which can easily be monitored by its characteristic fluorescence at 400 nm. The reactivity of tyrosine phenoxyl radical with O2 was examined by a variety of techniques. BT fluorescence was measured as a function of O2 concentration. Over a range of pH values (4-12) there was no effect of oxygen on BT production ([O2] less than or equal to 0.72 mM). In addition, oxygen uptake by the phenoxyl radical was measured directly with an oxygen electrode. It was determined by this technique that oxygen does not react with the phenoxyl radical with a rate constant greater than 10(3) M-1 s-1. Tyrosine phenoxyl radical "repair" by superoxide and physiological antioxidants was examined by BT fluorescence quenching as well as pulse radiolysis. Implications of these results as to the fate of tyrosine phenoxyl radicals produced in biological systems is discussed.
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For tyrosyl radicals, reaction with superoxide to form tyrosine hydroperoxide is three times faster than dimerization.
“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 [141]
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- Authors
- Hunter, E. P. L., Desrosiers, M. F., & Simic, M. G.
- Affiliations
- National Institute of Standards and Technology (US)
- Corresponding author
- Desrosiers, Marc F.
- Venue
- Free Radical Biology and Medicine
- Publisher
- Elsevier BV
- Published
- 1989
- Volume
- 6
- Issue
- 6
- Pages
- 581-585
- ISSN
- 0891-5849 (ISSN-L)
- OpenAlex
- W1994259078
- Cited by
- 153
- References
- 30
- Citations by year
- 2026: 4 · 2025: 1 · 2024: 4 · 2023: 4 · 2022: 2 · 2021: 6 · 2020: 5 · 2019: 3 · 2018: 8 · 2017: 4 · 2016: 10 · 2015: 1 · 2014: 3 · 2013: 2 · 2012: 6
- FWCI
- 5.39
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Free Radical Biology and Medicine (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Health Sciences › Medicine › Biochemistry › Antioxidant Activity and Oxidative Stress
- Keywords
- radical dimerization, superoxide, antioxidants, oxygen reactivity, oxygen consumption, fluorescence quenching, pulse radiolysis, pH dependence
- MeSH terms
- Antioxidants, Ascorbic Acid, Chromans, Free Radicals, Oxygen, Spectrometry, Fluorescence, Superoxides, Tyrosine
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