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Formation of [b3 - 1 + cat]+ ions from metal-cationized tetrapeptides containing beta-alanine, gamma-aminobutyric acid or epsilon-aminocaproic acid residues

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dc.contributor Wichita State University. Department of Chemistry en_US
dc.contributor.author Osburn, Sandra M. en_US
dc.contributor.author Ochola, Sila O. en_US
dc.contributor.author Talaty, Erach R. en_US
dc.contributor.author Van Stipdonk, Michael J. en_US
dc.date.accessioned 2012-02-06T17:16:30Z
dc.date.available 2012-02-06T17:16:30Z
dc.date.issued 2008-11-01 en_US
dc.identifier 18449851 en_US
dc.identifier 9504818 en_US
dc.identifier.citation Journal of mass spectrometry : JMS. 2008 Nov; 43(11): 1458-69. en_US
dc.identifier.issn 1076-5174 en_US
dc.identifier.uri http://dx.doi.org/10.1002/jms.1418 en_US
dc.identifier.uri http://hdl.handle.net/10057/4328
dc.description Click on the DOI link below to access the article (may not be free). en_US
dc.description.abstract The presence and position of a single beta-alanine (betaA), gamma-aminobutyric acid (gammaABu) or epsilon-aminocaproic acid (Cap) residue has been shown to have a significant influence on the formation of b(n)+ and y(n)+ product ions from a series of model, protonated peptides. In this study, we examined the effect of the same residues on the formation of analogous [b3 - 1 + cat]+ products from metal (Li+, Na+ and Ag+)-cationized peptides. The larger amino acids suppress formation of b3+ from protonated peptides with general sequence AAXG (where X = beta-alanine, gamma-aminobutyric acid or epsilon-aminocaproic acid), presumably because of the prohibitive effect of larger cyclic intermediates in the 'oxazolone' pathway. However, abundant [b3 - 1 + cat]+ products are generated from metal-cationized versions of AAXG. Using a group of deuterium-labeled and exchanged peptides, we found that formation of [b3 - 1 + cat]+ involves transfer of either amide or alpha-carbon position H atoms, and the tendency to transfer the atom from the alpha-carbon position increases with the size of the amino acid in position X. To account for the transfer of the H atom, a mechanism involving formation of a ketene product as [b3 - 1 + cat]+ is proposed. en_US
dc.format.extent 1458-69 en_US
dc.language.iso eng en_US
dc.publisher John Wiley and Sons en_US
dc.relation.ispartofseries Journal of mass spectrometry : JMS en_US
dc.relation.ispartofseries J Mass Spectrom en_US
dc.source NLM en_US
dc.subject Research Support, Non-U.S. Gov't en_US
dc.subject Research Support, U.S. Gov't, Non-P.H.S. en_US
dc.subject.mesh 6-Aminocaproic Acid/chemistry en_US
dc.subject.mesh Cations en_US
dc.subject.mesh Ions en_US
dc.subject.mesh Metals/chemistry en_US
dc.subject.mesh Peptides/chemistry en_US
dc.subject.mesh Spectrometry, Mass, Electrospray Ionization/methods en_US
dc.subject.mesh beta-Alanine/chemistry en_US
dc.subject.mesh gamma-Aminobutyric Acid/chemistry en_US
dc.title Formation of [b3 - 1 + cat]+ ions from metal-cationized tetrapeptides containing beta-alanine, gamma-aminobutyric acid or epsilon-aminocaproic acid residues en_US
dc.type Article en_US
dc.coverage.spacial England en_US
dc.description.version peer reviewed en_US
dc.rights.holder Copyright © 2008 John Wiley & Sons, Ltd. en_US

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