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

被引：110
作者：
Trujillo, Madia [1 ,2 ]
Alvarez, Beatriz [2 ,3 ]
Radi, Rafael [1 ,2 ]
机构：
[1] Univ Republica, Fac Med, Dept Bioquim, Montevideo, Uruguay
[2] Univ Republica, Ctr Free Radical & Biomed Res, Montevideo, Uruguay
[3] Univ Republica, Fac Ciencias, Lab Enzimol, Montevideo, Uruguay
来源：
FREE RADICAL RESEARCH | 2016年 / 50卷 / 02期
基金：
美国国家卫生研究院;
关键词：
Cysteine; peroxidases sulfenic acid; thiol; thiyl radical; PROTEIN-TYROSINE PHOSPHATASES; CARBONATE RADICAL-ANION; INTRAMOLECULAR ELECTRON-TRANSFER; PEROXYNITRITE REDUCTASE-ACTIVITY; CIS-TRANS ISOMERIZATION; SULFENIC ACID FORMATION; HYDROGEN-PEROXIDE; HYPOCHLOROUS ACID; NITRIC-OXIDE; RATE-CONSTANTS;
D O I：
10.3109/10715762.2015.1089988
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
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.
引用
收藏
页码：150 / 171
页数：22
相关论文
共 250 条
[1]   Extraordinary μs-ms backbone dynamics in Arabidopsis thaliana peroxiredoxin Q [J].
Aden, Jorgen ;
Wallgren, Marcus ;
Storm, Patrik ;
Weise, Christoph F. ;
Christiansen, Alexander ;
Schroder, Wolfgang P. ;
Funk, Christiane ;
Wolf-Watz, Magnus .
BIOCHIMICA ET BIOPHYSICA ACTA-PROTEINS AND PROTEOMICS, 2011, 1814 (12) :1880-1890
[2]   FORMATION OF A PROTEIN SULFENAMIDE DURING INACTIVATION OF ACYL PHOSPHATASE-ACTIVITY OF OXIDIZED GLYCERALDEHYDE-3-PHOSPHATE DEHYDROGENASE BY BENZYLAMINE [J].
ALLISON, WS ;
BENITEZ, LV ;
JOHNSON, CL .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1973, 52 (04) :1403-1409
[3]   The Reaction of Sulfenic Acids with Peroxyl Radicals: Insights into the Radical-Trapping Antioxidant Activity of Plant-Derived Thiosulfinates [J].
Amorati, Riccardo ;
Lynett, Philip T. ;
Valgimigli, Luca ;
Pratt, Derek A. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (20) :6370-6379
[4]   Thiol-Based Redox Switches and Gene Regulation [J].
Antelmann, Haike ;
Helmann, John D. .
ANTIOXIDANTS & REDOX SIGNALING, 2011, 14 (06) :1049-1063
[5]   First steps in the oxidation of sulfur-containing amino acids by hypohalogenation:: Very fast generation of intermediate sulfenyl halides and halosulfonium cations [J].
Armesto, XL ;
Canle, M ;
Fernández, MI ;
García, MV ;
Santaballa, JA .
TETRAHEDRON, 2000, 56 (08) :1103-1109
[6]   HYPOTHIOCYANITE [J].
Ashby, Michael T. .
ADVANCES IN INORGANIC CHEMISTRY, VOL 64: INORGANIC BIOINORGANIC REACTION MECHANISMS, 2012, 64 :263-303
[7]   Regulation of the OxyR transcription factor by hydrogen peroxide and the cellular thiol -: disulfide status [J].
Åslund, F ;
Zheng, M ;
Beckwith, J ;
Storz, G .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (11) :6161-6165
[8]   Redox potentials of glutaredoxins and other thiol-disulfide oxidoreductases of the thioredoxin superfamily determined by direct protein-protein redox equilibria [J].
Åslund, F ;
Berndt, KD ;
Holmgren, A .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1997, 272 (49) :30780-30786
[9]   EPR detection of glutathiyl and hemoglobin-cysteinyl radicals during the interaction of peroxynitrite with human erythrocytes [J].
Augusto, O ;
de Menezes, SL ;
Linares, E ;
Romero, N ;
Radi, R ;
Denicola, A .
BIOCHEMISTRY, 2002, 41 (48) :14323-14328
[10]   Nitrogen dioxide and carbonate radical anion: Two emerging radicals in biology [J].
Augusto, O ;
Bonini, MG ;
Amanso, AM ;
Linares, E ;
Santos, CCX ;
De Menezes, SL .
FREE RADICAL BIOLOGY AND MEDICINE, 2002, 32 (09) :841-859
12345678910