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Article: Methionine, α-methylmethionine and S-methylcysteine radical cations: Generations and dissociations in the gas phase

TitleMethionine, α-methylmethionine and S-methylcysteine radical cations: Generations and dissociations in the gas phase
Authors
Issue Date2009
PublisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/pccp
Citation
Physical Chemistry Chemical Physics, 2009, v. 11 n. 35, p. 7629-7639 How to Cite?
AbstractMethionine, α-methylmethionine and S-methylcysteine radical cations have been formed by oxidative dissociations of [Cu II(M)(CH 3CN) 2] 2+ complexes. The radical cations M + were trapped, and CID spectra (MS 3) of these ions are presented. Fragmentations of the methionine and S-methylcysteine radical cations, initiated by migration of the α-carbon hydrogen atom to the sulfur, trigger the losses of water and thiomethanol from methionine and thiomethanol from S-methylcysteine. Deuterium labeling experiments show that considerable H-D scrambling and rearrangements involving N-H and S-H hydrogens occur in the methionine radical cation prior to fragmentation. An additional channel for S-methylcysteine is the loss of ammonia following β-hydrogen migration. Methylation at the α-carbon of methionine results in a radical cation that fragments differently. Two neutral losses from α- methylmethionine, NH 3 and methyl vinyl sulfide, CH 2CH-S-CH 3, are initiated by γ-hydrogen migration; a third channel is the loss of COOH. DFT computations at the B3LYP/6-311++G(d,p) level have been used to test aspects of the proposed fragmentation mechanisms of the radical cations. © 2009 the Owner Societies.
Persistent Identifierhttp://hdl.handle.net/10722/168400
ISSN
2015 Impact Factor: 4.449
2015 SCImago Journal Rankings: 1.836
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorZhao, Jen_US
dc.contributor.authorNg, CMDen_US
dc.contributor.authorChu, IKen_US
dc.contributor.authorSiu, KWMen_US
dc.contributor.authorHopkinson, ACen_US
dc.date.accessioned2012-10-08T03:18:29Z-
dc.date.available2012-10-08T03:18:29Z-
dc.date.issued2009en_US
dc.identifier.citationPhysical Chemistry Chemical Physics, 2009, v. 11 n. 35, p. 7629-7639en_US
dc.identifier.issn1463-9076en_US
dc.identifier.urihttp://hdl.handle.net/10722/168400-
dc.description.abstractMethionine, α-methylmethionine and S-methylcysteine radical cations have been formed by oxidative dissociations of [Cu II(M)(CH 3CN) 2] 2+ complexes. The radical cations M + were trapped, and CID spectra (MS 3) of these ions are presented. Fragmentations of the methionine and S-methylcysteine radical cations, initiated by migration of the α-carbon hydrogen atom to the sulfur, trigger the losses of water and thiomethanol from methionine and thiomethanol from S-methylcysteine. Deuterium labeling experiments show that considerable H-D scrambling and rearrangements involving N-H and S-H hydrogens occur in the methionine radical cation prior to fragmentation. An additional channel for S-methylcysteine is the loss of ammonia following β-hydrogen migration. Methylation at the α-carbon of methionine results in a radical cation that fragments differently. Two neutral losses from α- methylmethionine, NH 3 and methyl vinyl sulfide, CH 2CH-S-CH 3, are initiated by γ-hydrogen migration; a third channel is the loss of COOH. DFT computations at the B3LYP/6-311++G(d,p) level have been used to test aspects of the proposed fragmentation mechanisms of the radical cations. © 2009 the Owner Societies.en_US
dc.languageengen_US
dc.publisherRoyal Society of Chemistry. The Journal's web site is located at http://www.rsc.org/pccpen_US
dc.relation.ispartofPhysical Chemistry Chemical Physicsen_US
dc.subject.meshCations - Chemistryen_US
dc.subject.meshCysteine - Analogs & Derivatives - Chemistryen_US
dc.subject.meshGases - Chemistryen_US
dc.subject.meshMethionine - Analogs & Derivatives - Chemistryen_US
dc.subject.meshModels, Molecularen_US
dc.titleMethionine, α-methylmethionine and S-methylcysteine radical cations: Generations and dissociations in the gas phaseen_US
dc.typeArticleen_US
dc.identifier.emailChu, IK:ivankchu@hku.hken_US
dc.identifier.authorityChu, IK=rp00683en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1039/b905615gen_US
dc.identifier.pmid19950502-
dc.identifier.scopuseid_2-s2.0-69649092350en_US
dc.identifier.hkuros180641-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-69649092350&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume11en_US
dc.identifier.issue35en_US
dc.identifier.spage7629en_US
dc.identifier.epage7639en_US
dc.identifier.isiWOS:000269400500014-
dc.publisher.placeUnited Kingdomen_US
dc.identifier.scopusauthoridZhao, J=8611619900en_US
dc.identifier.scopusauthoridNg, CMD=55107694700en_US
dc.identifier.scopusauthoridChu, IK=7103327484en_US
dc.identifier.scopusauthoridSiu, KWM=8967015800en_US
dc.identifier.scopusauthoridHopkinson, AC=15067169300en_US

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