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dc.contributor.author
Adam, Claudia Guadalupe
dc.contributor.author
García Río, Luis
dc.contributor.author
Leis, José Ramón
dc.contributor.author
Ribeiro, Lara
dc.date.available
2020-04-14T21:07:33Z
dc.date.issued
2005-08
dc.identifier.citation
Adam, Claudia Guadalupe; García Río, Luis; Leis, José Ramón; Ribeiro, Lara; Nitroso Group Transfer in S -Nitrosocysteine: Evidence of a New Decomposition Pathway for Nitrosothiols; American Chemical Society; Journal of Organic Chemistry; 70; 16; 8-2005; 6353-6361
dc.identifier.issn
0022-3263
dc.identifier.uri
http://hdl.handle.net/11336/102573
dc.description.abstract
<span lang="en">
<p class="MsoNormal" style="MARGIN: 0cm 0cm 0pt 18pt; TEXT-ALIGN: justify; mso-layout-grid-align: none"><span lang="en" style="FONT-SIZE: 9.5pt; FONT-FAMILY: Arial; mso-ansi-language: EN-GB">The rate of <i>S</i>-nitrosocysteine decomposition in a pH range between 0.7 < pH < 13 exhibits firstand second-order dependence on total cysteine concentration. The second-order term is only observed for pH values between 6.9 < pH < 12. Both first- and second-order terms show a complex dependence on the acidity of the medium. They increase with increasing pH, reaching a maximum value around pH ) 8 and then decrease with further increase in pH. An analysis of the reaction products reveals the absence of nitrite ion and ammonia. No evidence of catalysis by copper ions is observed. These results suggest the existence of a new decomposition pathway for <i>S</i>-nitrosocysteine, which proceeds via an intramolecular nitroso group transfer producing a primary <i>N</i>-nitrosamine that decomposes rapidly to give the corresponding diazonium salt. The nitroso group transfer reaction occurs intermolecularly for the decomposition pathway exhibiting a quadratic dependence on cysteine concentration. Both nitroso group transfer pathways are subject to acid catalysis by cysteine. Kinetic results indicate that the extent of S‚‚‚NO bond cleavage in the transition state is ahead of protonation of the AH‚‚‚S sulfur atom. The results obtained show the existence of a new decomposition pathway for the <i>S</i>-nitrosocysteine where NO is not released, and hence, it has a significant biological impact due to the potential use of nitrosothiols as NO donors.</span><span lang="en" style="FONT-SIZE: 10pt; FONT-FAMILY: Arial; mso-ansi-language: EN-GB">
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dc.format
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject.classification
Físico-Química, Ciencia de los Polímeros, Electroquímica
dc.subject.classification
Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
Nitroso Group Transfer in S -Nitrosocysteine: Evidence of a New Decomposition Pathway for Nitrosothiols
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2020-04-13T13:18:20Z
dc.journal.volume
70
dc.journal.number
16
dc.journal.pagination
6353-6361
dc.journal.pais
Estados Unidos
dc.journal.ciudad
Washington DC
dc.description.fil
Fil: Adam, Claudia Guadalupe. Universidad Nacional del Litoral. Facultad de Ingeniería Química; Argentina. Universidad de Santiago de Compostela; España. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Santa Fe; Argentina
dc.description.fil
Fil: García Río, Luis. Universidad de Santiago de Compostela; España
dc.description.fil
Fil: Leis, José Ramón. Universidad de Santiago de Compostela; España
dc.description.fil
Fil: Ribeiro, Lara. Universidad de Santiago de Compostela; España
dc.journal.title
Journal of Organic Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1021/jo050811r
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/jo050811r
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