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dc.contributorWichita State University. Department of Chemistryen_US
dc.contributor.authorAnbalagan, Victoren_US
dc.contributor.authorPatel, J. N.en_US
dc.contributor.authorNiyakorn, G.en_US
dc.contributor.authorVan Stipdonk, Michael J.en_US
dc.date.accessioned2012-02-06T17:16:19Z
dc.date.available2012-02-06T17:16:19Z
dc.date.issued2003-01-01en_US
dc.identifier12569438en_US
dc.identifier8802365en_US
dc.identifier.citationRapid communications in mass spectrometry : RCM. 2003; 17(4): 291-300.en_US
dc.identifier.issn0951-4198en_US
dc.identifier.urihttp://dx.doi.org/10.1002/rcm.912en_US
dc.identifier.urihttp://hdl.handle.net/10057/4322
dc.descriptionClick on the DOI link below to access the article (may not be free).en_US
dc.description.abstractIn this study we investigated the multi-stage collision-induced dissociation (CID) of N-terminally acetylated di-, tri- and tetrapeptides in the form of C-terminal ethyl, n-propyl, isopropyl, n-butyl and tert-butyl esters and cationized by the attachment of Li(+), Na(+) and Ag(+). While methyl ester versions of the metal cationized peptides primarily eliminate H(2)O following collisional activation and dissociation, the ethyl, propyl and butyl ester versions of the peptides exhibit a dissociation pathway consistent with gamma-hydrogen transfer to the C-terminal carbonyl group, with associated elimination of an alkene, in a McLafferty-type rearrangement. The rearrangement leaves a metal cationized, free-acid form of the peptide, as confirmed by comparing the multi-stage CID of rearrangement products generated from peptide esters with the CID of corresponding metal cationized free-acid peptides. The transfer of a gamma-hydrogen in the rearrangement reaction was confirmed by investigating the CID of ethyl esters for which the terminal methyl group was labeled with deuterium. We found that the rearrangement product was significantly more abundant, relative to other product ions, when derived from isopropyl and tert-butyl esters than from ethyl, n-propyl or n-butyl ester analogues.en_US
dc.format.extent291-300en_US
dc.language.isoengen_US
dc.publisherJohn Wiley and Sonsen_US
dc.relation.ispartofseriesRapid communications in mass spectrometry : RCMen_US
dc.relation.ispartofseriesRapid Commun. Mass Spectrom.en_US
dc.sourceNLMen_US
dc.subjectResearch Support, Non-U.S. Gov'ten_US
dc.subjectResearch Support, U.S. Gov't, Non-P.H.S.en_US
dc.subject.meshAcetylationen_US
dc.subject.meshCations, Monovalent/chemistryen_US
dc.subject.meshEsterificationen_US
dc.subject.meshEsters/chemistryen_US
dc.subject.meshLithium/chemistryen_US
dc.subject.meshMolecular Structureen_US
dc.subject.meshPeptides/chemistryen_US
dc.subject.meshSilver/chemistryen_US
dc.subject.meshSodium/chemistryen_US
dc.subject.meshSpectrometry, Mass, Electrospray Ionizationen_US
dc.titleMcLafferty-type rearrangement in the collision-induced dissociation of Li+, Na+ and Ag+ cationized esters of N-acetylated peptidesen_US
dc.typeArticleen_US
dc.coverage.spacialEnglanden_US
dc.description.versionpeer revieweden_US
dc.rights.holderCopyright © 2003 John Wiley & Sons, Ltd.en_US


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