Journal
JOURNAL OF CHROMATOGRAPHY A
Volume 1216, Issue 43, Pages 7205-7212Publisher
ELSEVIER
DOI: 10.1016/j.chroma.2009.08.054
Keywords
LC-MS; Ion trap; Tandem mass spectrometry; Maillard reaction; Glycated peptides; Gastrointestinal digestion
Funding
- Ministerio de Educacion y Ciencia [CSD2007-00063]
- Comunidad de Madrid [ALIBIRD S-0505/AGR/000153, ANALYSIC S-505/AGR-0312]
- CSIC [SIALOBIOTIC PIF-200870F0101]
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This article describes a comprehensive characterization of bovine beta-lactoglobulin peptides glycated with an aldohexose (galactose) or a ketohexose (tagatose), derived from in vitro gastrointestinal digestion, by liquid chromatography coupled to positive electrospray ion trap tandem mass spectrometry. In addition to the dissociation pathway previously described for aldohexoses-derived Amadori compounds, i.e. formation of the pyrylium ([M+H](+)-54) and furylium ions ([M+H](+)-84) via the oxonium ion ([M+H](+)-18), another and more direct fragmentation route involving the formation of the imminium ion ([M+H](+)-150) is also reported following extensive glycation rates of P-lactoglobulin with both carbohydrates. These results indicated that the analysis of digested proteins by LC-ESI-MS2 oil a three-dimensional ion trap monitoring neutral losses is an efficient and direct method to identify peptides glycated not only through the Amadori rearrangement but also via the Heyns rearrangement. Nevertheless, as the predominating MS2 fragmentation pattern of the glycated peptides is derived from the sugar moiety, the sequence-informative b- and y-ions resulting from peptide backbone cleavage were undetected. To overcome this drawback, and taking advantage of multi-stage fragmentation capabilities of ion traps, the indicative Amadori and Heyns-derived imminium ions were Successfully used in MS3 analyses to identify the peptide backbone, as well as the specific glycation site. In addition, further MS4 analyses were needed to carry Out the characterization of doubly glycated peptides. (C) 2009 Elsevier B.V. All rights reserved.
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