Cited by 142Redox biology and oxidative stressFree Radicals and AntioxidantsSulfur Compounds in Biology

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One- and two-electron oxidation of thiols: mechanisms, kinetics and biological fates

Trujillo, Madia, Alvarez, Beatriz, Radi, Rafael·2016·Free Radical Research

DOI 10.3109/10715762.2015.1089988

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Abstract

The oxidation of biothiols participates not only in the defense against oxidative damage but also in enzymatic catalytic mechanisms and signal transduction processes. Thiols are versatile reductants that react with oxidizing species by one- and two-electron mechanisms, leading to thiyl radicals and sulfenic acids, respectively. These intermediates, depending on the conditions, participate in further reactions that converge on different stable products. Through this review, we will describe the biologically relevant species that are able to perform these oxidations and we will analyze the mechanisms and kinetics of the one- and two-electron reactions. The processes undergone by typical low-molecular-weight thiols as well as the particularities of specific thiol proteins will be described, including the molecular determinants proposed to account for the extraordinary reactivities of peroxidatic thiols. Finally, the main fates of the thiyl radical and sulfenic acid intermediates will be summarized.

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Authors: Trujillo, M., Alvarez, B., & Radi, R.
Affiliations: Universidad de la República de Uruguay (UY)
Corresponding author: Trujillo, Madia
ORCID: Trujillo, Madia
Venue: Free Radical Research
Publisher: Informa UK Limited
Published: 2015-11-11
Volume: 50
Issue: 2
Pages: 150-171
ISSN: 1029-2470 (ISSN-L)
1071-5762
DOI: 10.3109/10715762.2015.1089988
OpenAlex: W1957064683
Cited by: 142
References: 254
Citations by year: 2026: 8 · 2025: 10 · 2024: 14 · 2023: 10 · 2022: 17 · 2021: 13 · 2020: 13 · 2019: 12 · 2018: 19 · 2017: 14 · 2016: 11 · 2015: 1
FWCI: 1.45
Type: journal article
Language: en
Open access: closed
Locations: Free Radical Research (publishedVersion)
PubMed (publishedVersion)
Funders: National Institute of Allergy and Infectious Diseases (R01AI095173)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Sulfur Compounds in Biology
Keywords: thiol oxidation, one-electron oxidation, two-electron oxidation, thiyl radicals, sulfenic acid, oxidation mechanism, reaction kinetics, thiol proteins, enzyme catalysis, signal transduction, thiol reductants
MeSH terms: Animals, Bacteria, Free Radicals, Humans, Kinetics, Oxidation-Reduction, Sulfenic Acids, Sulfhydryl Compounds, Eukaryota

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One- and two-electron oxidation of thiols: mechanisms, kinetics and biological fates

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