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    A study of the elimination of water from lithium-cationized tripeptide methyl esters by means of tandem mass spectrometry and isotope labeling

    Date
    2006-01-01
    Author
    Talaty, Erach R.
    Cooper, Travis J.
    Piland, Debra L.
    Bateman, David J.
    Syed, Adeel
    Stevenson, William T.K.
    Van Stipdonk, Michael J.
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    Citation
    Rapid communications in mass spectrometry : RCM. 2006; 20(20): 3007-17.
    Abstract
    Extensive isotope labeling (2H, 13C and 15N), collision-induced dissociation (CID) and multiple-stage tandem mass spectrometry were used to investigate the elimination of H2O from a series of model, metal-cationized tripeptide methyl esters. The present results corroborate our earlier suggestion that loss of water from lithiated peptides is initiated by a nucleophilic attack from the N-terminal side upon an amide carbonyl carbon atom to form a five-membered ring as an intermediate followed by 1,2-elimination of water. We show that the nucleophilic atom is the oxygen atom of the N-terminal amide group in the fragmentation of [AcGGGOMe+Li]+ as well as [GGGOMe+Li]+. However, the subsequent fragmentation is markedly different in the two cases as a result of the absence and presence of a free amino group. In particular, extensive scrambling of protons in the alpha-positions of GGGOMe is observed, presumably as a consequence of intervention of the basic amino group.
    Description
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    URI
    http://dx.doi.org/10.1002/rcm.2694
    http://hdl.handle.net/10057/4227
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