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Suarez, S.A.; Muñoz, M.; Alvarez, L.; Venâncio, M.F.; Rocha, W.R.; Bikiel, D.E.; Marti, M.A.; Doctorovich, F. "HNO Is Produced by the Reaction of NO with Thiols" (2017) Journal of the American Chemical Society. 139(41):14483-14487
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Abstract:

Azanone (nitroxyl, HNO) is a highly reactive compound whose biological role is still a matter of debate. One possible route for its formation is NO reduction by biological reductants. These reactions have been historically discarded due to the negative redox potential for the NO,H+/HNO couple. However, the NO to HNO conversion mediated by vitamins C, E, and aromatic alcohols has been recently shown to be feasible from a chemical standpoint. Based on these precedents, we decided to study the reaction of NO with thiols as potential sources of HNO. Using two complementary approaches, trapping by a Mn porphyrin and an HNO electrochemical sensor, we found that under anaerobic conditions aliphatic and aromatic thiols (as well as selenols) are able to convert NO to HNO, albeit at different rates. Further mechanistic analysis using ab initio methods shows that the reaction between NO and the thiol produces a free radical adduct RSNOH•, which reacts with a second NO molecule to produce HNO and a nitrosothiol. The nitrosothiol intermediate reacts further with RSH to produce a second molecule of HNO and RSSR, as previously reported. © 2017 American Chemical Society.

Registro:

Documento: Artículo
Título:HNO Is Produced by the Reaction of NO with Thiols
Autor:Suarez, S.A.; Muñoz, M.; Alvarez, L.; Venâncio, M.F.; Rocha, W.R.; Bikiel, D.E.; Marti, M.A.; Doctorovich, F.
Filiación:Departamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, INQUIMAE-CONICET, Ciudad Universitaria, Buenos Aires, C1428EHA, Argentina
Departamento de Química, Universidade Federal de Minas Gerais, Belo Horizonte, 31270-901, Brazil
Departamento de Química Biológica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, IQUIBICEN-CONICET, Ciudad Universitaria, Buenos Aires, C1428EHA, Argentina
Palabras clave:Aromatic compounds; Free radicals; Manganese; Molecules; Ab initio method; Anaerobic conditions; Aromatic alcohols; Aromatic thiol; Mechanistic analysis; Mn porphyrins; Potential sources; Redox potentials; Redox reactions; alpha tocopherol; ascorbic acid; azanone; hydroquinone; manganese; nitric oxide; nitroxyl; thiol derivative; tyrosine; unclassified drug; ab initio calculation; Article; chemical reaction; controlled study; density functional theory; dimerization; nuclear magnetic resonance spectroscopy; nucleophilicity; oxidation reduction potential; proton transport; rate constant; tautomer
Año:2017
Volumen:139
Número:41
Página de inicio:14483
Página de fin:14487
DOI: http://dx.doi.org/10.1021/jacs.7b06968
Título revista:Journal of the American Chemical Society
Título revista abreviado:J. Am. Chem. Soc.
ISSN:00027863
CODEN:JACSA
CAS:alpha tocopherol, 1406-18-4, 1406-70-8, 52225-20-4, 58-95-7, 59-02-9; ascorbic acid, 134-03-2, 15421-15-5, 50-81-7; hydroquinone, 123-31-9; manganese, 16397-91-4, 7439-96-5; nitric oxide, 10102-43-9; thiol derivative, 13940-21-1; tyrosine, 16870-43-2, 55520-40-6, 60-18-4
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00027863_v139_n41_p14483_Suarez

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Citas:

---------- APA ----------
Suarez, S.A., Muñoz, M., Alvarez, L., Venâncio, M.F., Rocha, W.R., Bikiel, D.E., Marti, M.A.,..., Doctorovich, F. (2017) . HNO Is Produced by the Reaction of NO with Thiols. Journal of the American Chemical Society, 139(41), 14483-14487.
http://dx.doi.org/10.1021/jacs.7b06968
---------- CHICAGO ----------
Suarez, S.A., Muñoz, M., Alvarez, L., Venâncio, M.F., Rocha, W.R., Bikiel, D.E., et al. "HNO Is Produced by the Reaction of NO with Thiols" . Journal of the American Chemical Society 139, no. 41 (2017) : 14483-14487.
http://dx.doi.org/10.1021/jacs.7b06968
---------- MLA ----------
Suarez, S.A., Muñoz, M., Alvarez, L., Venâncio, M.F., Rocha, W.R., Bikiel, D.E., et al. "HNO Is Produced by the Reaction of NO with Thiols" . Journal of the American Chemical Society, vol. 139, no. 41, 2017, pp. 14483-14487.
http://dx.doi.org/10.1021/jacs.7b06968
---------- VANCOUVER ----------
Suarez, S.A., Muñoz, M., Alvarez, L., Venâncio, M.F., Rocha, W.R., Bikiel, D.E., et al. HNO Is Produced by the Reaction of NO with Thiols. J. Am. Chem. Soc. 2017;139(41):14483-14487.
http://dx.doi.org/10.1021/jacs.7b06968