Identification of protein-derived tyrosyl radical in the reaction of cytochrome c and hydrogen peroxide: characterization by ESR spin-trapping, HPLC and MS

The Biochemical Journal
Steven Y QianRonald P Mason

Abstract

The reaction of cytochrome c and H(2)O(2) is known to form a protein-centred radical that can be detected with the spin trap 2-methyl-2-nitrosopropane (MNP). To characterize the MNP/tyrosyl adduct structure that had previously been determined incorrectly [Barr, Gunther, Deterding, Tomer and Mason (1996) J. Biol. Chem. 271, 15498-15503], we eliminated unreasonable structure models by ESR studies with a series of (13)C-labelled tyrosines, and photochemically synthesized an authentic MNP/tyrosyl adduct that has its trapping site on the C-3 position of the tyrosine phenyl ring. The observation of the identical ESR spectra for this radical adduct from the UV irradiation of 3-iodo-tyrosine and the adduct from the cytochrome c reaction demonstrated that the radical trapping site of MNP/tyrosyl is located on the equivalent C-3/C-5 positions instead of the C-1 position, as was proposed by Barr et al. In an on-line HPLC/ESR system, an identical retention time (17.7 min) was observed for the ESR-active HPLC peak of the MNP/tyrosyl adduct from the following three reactions: (i) the tyrosine oxidation via horseradish peroxidase/H(2)O(2); (ii) UV irradiation of 3-iodo-tyrosine and (iii) the reaction of cytochrome c with H(2)O(2). This result...Continue Reading

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Citations

Apr 15, 2004·Free Radical Biology & Medicine·Michael J Davies, Clare L Hawkins
Oct 30, 2003·Free Radical Biology & Medicine·Jianfei JiangValerian E Kagan
Feb 25, 2011·ACS Nano·Gregg P KotcheyAlexander Star
Oct 13, 2011·Nature Communications·Jeffrey AtkinsonValerian E Kagan
Dec 23, 2008·Antioxidants & Redox Signaling·Gloria Saab-Rincón, Brenda Valderrama
Oct 3, 2006·Biochemistry. Biokhimii︠a︡·Yu A VladimirovV E Kagan
Apr 10, 2013·Biochimica Et Biophysica Acta·Clare L Hawkins, Michael J Davies
Dec 19, 2003·Biochemical and Biophysical Research Communications·Sang Mok Kim, Sanghwa Han
Aug 28, 2015·PloS One·Juliana C FerreiraIseli L Nantes
Jan 4, 2008·The Journal of Biological Chemistry·Gundars GoldsteinsJari Koistinaho
Jul 12, 2003·The Journal of Biological Chemistry·Olivier M Lardinois, Paul R Ortiz de Montellano
Jun 7, 2002·The Journal of Biological Chemistry·Yeong-Renn ChenRonald P Mason
Oct 20, 2017·Journal of the American Chemical Society·Victor YinLars Konermann
Mar 17, 2009·Free Radical Biology & Medicine·Valerian E KaganGrigory Borisenko

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