HNO is produced by the reaction of NO with thiols

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dc.creatorSebastián Angel Suárez
dc.creatorMartina Muñoz
dc.creatorLucia Alvarez
dc.creatorMateus Fernandes Venâncio
dc.creatorWillian Ricardo Rocha
dc.creatorDamian Ezequiel Bikiel
dc.creatorMarcelo A. Marti
dc.creatorFabio Doctorovich
dc.date.accessioned2023-02-23T15:09:39Z
dc.date.accessioned2025-09-09T01:19:50Z
dc.date.available2023-02-23T15:09:39Z
dc.date.issued2017
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipOutra Agência
dc.identifier.doihttps://doi.org/10.1021/jacs.7b06968
dc.identifier.issn1520-5126
dc.identifier.urihttps://hdl.handle.net/1843/50318
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.rightsAcesso Restrito
dc.subjectCompostos aromáticos
dc.subjectMoléculas
dc.subjectMonômeros
dc.subjectPeptídeos
dc.subjectProteínas
dc.subjectTióis
dc.subjectMecânica quântica
dc.subjectMétodo de Monte Carlo
dc.subject.otherAromatic compounds
dc.subject.otherMolecules
dc.subject.otherMonomers
dc.subject.otherPeptides and proteins
dc.subject.otherThiols
dc.titleHNO is produced by the reaction of NO with thiols
dc.typeArtigo de periódico
local.citation.epage14487
local.citation.issue41
local.citation.spage14483
local.citation.volume139
local.description.resumoAzanone (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.
local.identifier.orcidhttps://orcid.org/0000-0003-0236-5743
local.identifier.orcidhttps://orcid.org/0000-0002-8088-447X
local.identifier.orcidhttps://orcid.org/0000-0002-0025-2158
local.identifier.orcidhttps://orcid.org/0000-0002-7911-9340
local.identifier.orcidhttps://orcid.org/0000-0003-1088-2089
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://pubs.acs.org/doi/10.1021/jacs.7b06968

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