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Abstract:

Experimental studies in hemeproteins and model Tyr/Cys-containing peptides exposed to oxidizing and nitrating species suggest that intramolecular electron transfer (IET) between tyrosyl radicals (Tyr-O) and Cys residues controls oxidative modification yields. The molecular basis of this IET process is not sufficiently understood with structural atomic detail. Herein, we analyzed using molecular dynamics and quantum mechanics-based computational calculations, mechanistic possibilities for the radical transfer reaction in Tyr/Cys-containing peptides in solution and correlated them with existing experimental data. Our results support that Tyr-O to Cys radical transfer is mediated by an acid/base equilibrium that involves deprotonation of Cys to form the thiolate, followed by a likely rate-limiting transfer process to yield cysteinyl radical and a Tyr phenolate; proton uptake by Tyr completes the reaction. Both, the pKa values of the Tyr phenol and Cys thiol groups and the energetic and kinetics of the reversible IET are revealed as key physico-chemical factors. The proposed mechanism constitutes a case of sequential, acid/base equilibrium-dependent and solvent-mediated, proton-coupled electron transfer and explains the dependency of oxidative yields in Tyr/Cys peptides as a function of the number of alanine spacers. These findings contribute to explain oxidative modifications in proteins that contain sequence and/or spatially close Tyr-Cys residues. © 2012 Elsevier Inc. All rights reserved.

Registro:

Documento: Artículo
Título:Molecular basis of intramolecular electron transfer in proteins during radical-mediated oxidations: Computer simulation studies in model tyrosine-cysteine peptides in solution
Autor:Petruk, A.A.; Bartesaghi, S.; Trujillo, M.; Estrin, D.A.; Murgida, D.; Kalyanaraman, B.; Marti, M.A.; Radi, R.
Filiación:Instituto Superior de Investigaciones Biológicas (CONICET-UNT), S.M. de Tucumán, Chacabuco 461, Tucumán, T4000CAN, Argentina
Instituto de Química Del Noroeste Argentino (CONICET-UNT), S.M. de Tucumán, Ayacucho 471, Tucumán, T4000CAN, Argentina
Departamento de Histología, Universidad de la República, Uruguay
Departamento de Bioquímica, Facultad de Medicina, Universidad de la República, Avda. General Flores 2125, 11800 Montevideo, Uruguay
Center for Free Radical and Biomedical Research, Facultad de Medicina, Universidad de la República, Uruguay
Departamento de Química Inorgánica, Analítica y Química Física, INQUIMAE-CONICET, Argentina
Department of Biophysics, Medical College of Wisconsin, Milwaukee, WI, United States
Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Buenos Aires, C1428EHA, Argentina
Palabras clave:Computer simulation; Electron transfer; Nitration; Oxidation; Tyrosyl radical; alanine; cysteine; hydrogen; phenol derivative; thiol derivative; tyrosine; water; acid base balance; amino acid sequence; article; chemical reaction kinetics; chemical structure; computer simulation; electron transport; hydrogen bond; molecular dynamics; oxidation; physical chemistry; priority journal; protein conformation; protein modification; protein structure; proton transport; quantum mechanics; solvation; thermodynamics; Computer Simulation; Cysteine; Electron Transport; Free Radicals; Kinetics; Molecular Dynamics Simulation; Peptides; Proteins; Quantum Theory; Solutions; Tyrosine; Water
Año:2012
Volumen:525
Número:1
Página de inicio:82
Página de fin:91
DOI: http://dx.doi.org/10.1016/j.abb.2012.05.012
Título revista:Archives of Biochemistry and Biophysics
Título revista abreviado:Arch. Biochem. Biophys.
ISSN:00039861
CODEN:ABBIA
CAS:alanine, 56-41-7, 6898-94-8; cysteine, 4371-52-2, 52-89-1, 52-90-4; hydrogen, 12385-13-6, 1333-74-0; thiol derivative, 13940-21-1; tyrosine, 16870-43-2, 55520-40-6, 60-18-4; water, 7732-18-5; Cysteine, 52-90-4; Free Radicals; Peptides; Proteins; Solutions; Tyrosine, 55520-40-6; Water, 7732-18-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00039861_v525_n1_p82_Petruk

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Citas:

---------- APA ----------
Petruk, A.A., Bartesaghi, S., Trujillo, M., Estrin, D.A., Murgida, D., Kalyanaraman, B., Marti, M.A.,..., Radi, R. (2012) . Molecular basis of intramolecular electron transfer in proteins during radical-mediated oxidations: Computer simulation studies in model tyrosine-cysteine peptides in solution. Archives of Biochemistry and Biophysics, 525(1), 82-91.
http://dx.doi.org/10.1016/j.abb.2012.05.012
---------- CHICAGO ----------
Petruk, A.A., Bartesaghi, S., Trujillo, M., Estrin, D.A., Murgida, D., Kalyanaraman, B., et al. "Molecular basis of intramolecular electron transfer in proteins during radical-mediated oxidations: Computer simulation studies in model tyrosine-cysteine peptides in solution" . Archives of Biochemistry and Biophysics 525, no. 1 (2012) : 82-91.
http://dx.doi.org/10.1016/j.abb.2012.05.012
---------- MLA ----------
Petruk, A.A., Bartesaghi, S., Trujillo, M., Estrin, D.A., Murgida, D., Kalyanaraman, B., et al. "Molecular basis of intramolecular electron transfer in proteins during radical-mediated oxidations: Computer simulation studies in model tyrosine-cysteine peptides in solution" . Archives of Biochemistry and Biophysics, vol. 525, no. 1, 2012, pp. 82-91.
http://dx.doi.org/10.1016/j.abb.2012.05.012
---------- VANCOUVER ----------
Petruk, A.A., Bartesaghi, S., Trujillo, M., Estrin, D.A., Murgida, D., Kalyanaraman, B., et al. Molecular basis of intramolecular electron transfer in proteins during radical-mediated oxidations: Computer simulation studies in model tyrosine-cysteine peptides in solution. Arch. Biochem. Biophys. 2012;525(1):82-91.
http://dx.doi.org/10.1016/j.abb.2012.05.012