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Influence of a ring substituent on the tendency to form H(2)O adducts to Ag(+) complexes with phenylalanine analogues in an ion trap mass spectrometer

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dc.contributor Wichita State University. Department of Chemistry en_US
dc.contributor.author Perera, B. A. en_US
dc.contributor.author Gallardo, A. L. en_US
dc.contributor.author Barr, J. M. en_US
dc.contributor.author Tekarli, S. M. en_US
dc.contributor.author Anbalagan, Victor en_US
dc.contributor.author Talaty, Erach R. en_US
dc.contributor.author Van Stipdonk, Michael J. en_US
dc.date.accessioned 2012-02-06T17:15:21Z
dc.date.available 2012-02-06T17:15:21Z
dc.date.issued 2002-04-01 en_US
dc.identifier 11948847 en_US
dc.identifier 9504818 en_US
dc.identifier 10.1002/jms.296 en_US
dc.identifier.citation Journal of mass spectrometry : JMS. 2002 Apr; 37(4): 401-13. en_US
dc.identifier.issn 1076-5174 en_US
dc.identifier.uri http://dx.doi.org/10.1002/jms.296 en_US
dc.identifier.uri http://hdl.handle.net/10057/4228
dc.description Click on the DOI link below to access the article (may not be free). en_US
dc.description.abstract In a previous report we showed that certain binary Ag(+)-amino acid complexes formed adduct ions by the attachment of a single water and methanol molecule when stored in an ion trap mass spectrometer: complexes with aliphatic amino acids and with 4-fluorophenylalanine formed the adduct ions whereas complexes with phenylalanine and tryptophan did not. In this study we compared the tendency of the Ag(+) complexes derived from phenylalanine, 4-fluorophenylalanine, 4-hydroxyphenylalanine (tyrosine), 4-bromophenylalanine, 4-nitrophenylalanine and aminocyclohexanepropionic acid to form water adducts when stored, without further activation, in the ion trap for times ranging from 1 to 500 ms. Because the donation of pi electron density to the Ag(+) ion is a likely determining factor in complex reactivity, our aim in the present study was to determine qualitatively the influence of para-position substituents on the aromatic ring on the formation of the water adducts. Our results show that the reactivity of the complexes is influenced significantly by the presence of the various substituents. Decreases in [M + Ag](+) ion abundance, and increases in adduct ion abundance, both measured as a function of storage time, follow the trend -NO(2) > -Br > -F > -OH > -H. The complex of Ag(+) with 4-nitrophenylalanine was nearly as reactive towards water as the Ag(+) complex with aminocyclohexanepropionic acid, the last being an amino acid devoid of pi character in the ring system. Collision induced dissociation of the [M + Ag](+) species derived from the amino acids produces, among other products, Ag(+) complexes with a para-substituted phenylacetaldehyde: complexes that also form adduct species when stored in the ion trap. The trends in adduct ion formation exhibited by the aldehyde-Ag(+) complex ions were similar to those observed for the precursor complexes of Ag(+) and the amino acids, confirming the influence of the ring substituent. en_US
dc.format.extent 401-13 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 Comparative Study en_US
dc.subject Research Support, Non-U.S. Gov't en_US
dc.subject.mesh Cations, Divalent/chemistry en_US
dc.subject.mesh Molecular Conformation en_US
dc.subject.mesh Phenylalanine/analogs & derivatives en_US
dc.subject.mesh Silver/chemistry en_US
dc.subject.mesh Spectrometry, Mass, Electrospray Ionization en_US
dc.subject.mesh Water/chemistry en_US
dc.subject.mesh Phenylalanine/chemistry en_US
dc.title Influence of a ring substituent on the tendency to form H(2)O adducts to Ag(+) complexes with phenylalanine analogues in an ion trap mass spectrometer en_US
dc.type Article en_US
dc.coverage.spacial England en_US
dc.description.version peer reviewed en_US
dc.rights.holder Copyright © 2002 John Wiley & Sons, Ltd. en_US

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