ArticleJournal of the American Society for Mass Spectrometry2011
Structure and reactivity of the N-acetyl-cysteine radical cation and anion: does radical migration occur?
Article in Journal of the American Society for Mass Spectrometry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- w-Type ions formed by electron transfer dissociation of Cys-containing peptides investigated by infrared ion spectroscopy.Journal of mass spectrometry : JMS · 2018Article
- Near-UV Photodissociation of Tryptic Peptide Cation Radicals. Scope and Effects of Amino Acid Residues and Radical Sites.Journal of the American Society for Mass Spectrometry · 2017Article
- TEMPO-Assisted Free Radical-Initiated Peptide Sequencing Mass Spectrometry (FRIPS MS) in Q-TOF and Orbitrap Mass Spectrometers: Single-Step Peptide Backbone Dissociations in Positive Ion Mode.Journal of the American Society for Mass Spectrometry · 2017Article
- Characterization of a DAPI-RIT-DAPI system for gas-phase ion/molecule and ion/ion reactions.Journal of the American Society for Mass Spectrometry · 2014Article
- Gas-phase reactivity of peptide thiyl (RS•), perthiyl (RSS•), and sulfinyl (RSO•) radical ions formed from atmospheric pressure ion/radical reactions.Journal of the American Society for Mass Spectrometry · 2013Article
- Structure and reactivity of the distonic and aromatic radical cations of tryptophan.Journal of the American Society for Mass Spectrometry · 2013Article
- The radical ion chemistry of S-nitrosylated peptides.Journal of the American Society for Mass Spectrometry · 2012Article
- Gas-phase peptide sulfinyl radical ions: formation and unimolecular dissociation.Journal of the American Society for Mass Spectrometry · 2012Article
- Intramolecular hydrogen transfer reactions of thiyl radicals from glutathione: formation of carbon-centered radical at Glu, Cys, and Gly.Chemical research in toxicology · 2012Article
- S-to-αC radical migration in the radical cations of Gly-Cys and Cys-Gly.Journal of the American Society for Mass Spectrometry · 2012Article
- Reversible hydrogen transfer reactions in thiyl radicals from cysteine and related molecules: absolute kinetics and equilibrium constants determined by pulse radiolysis.The journal of physical chemistry. B · 2012Article
- Electron transfer dissociation (ETD) of peptides containing intrachain disulfide bonds.Journal of the American Society for Mass Spectrometry · 2012Article
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5 authors.
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Abstract
The structure and reactivity of the N-acetyl-cysteine radical cation and anion were studied using ion-molecule reactions, infrared multi-photon dissociation (IRMPD) spectroscopy, and density functional theory (DFT) calculations. The radical cation was generated by first nitrosylating the thiol of N-acetyl-cysteine followed by the homolytic cleavage of the S-NO bond in the gas phase. IRMPD spectroscopy coupled with DFT calculations revealed that for the radical cation the radical migrates from its initial position on the sulfur atom to the α-carbon position, which is 2.5 kJ mol(-1) lower in energy. The radical migration was confirmed by time-resolved ion-molecule reactions. These results are in contrast with our previous study on cysteine methyl ester radical cation (Osburn et al., Chem. Eur. J. 2011, 17, 873-879) and the study by Sinha et al. for cysteine radical cation (Phys. Chem. Chem. Phys. 2010, 12, 9794-9800) where the radical was found to stay on the sulfur atom as formed. A similar approach allowed us to form a hydrogen-deficient radical anion of N-acetyl-cysteine, (M - 2H)( •- ). IRMPD studies and ion-molecule reactions performed on the radical anion showed that the radical remains on the sulfur, which is the initial and more stable (by 63.6 kJ mol(-1)) position, and does not rearrange.
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