Peptide-phospholipid cross-linking reactions: identification of leucine enkephalin-alka(e)nal-glycerophosphatidylcholine adducts by tandem mass spectrometry

Journal of the American Society for Mass Spectrometry
A ReisM R M Domingues

Abstract

The covalent interactions between peptides and lipid oxidation products, with formation of Schiff and Michael adducts, are known to occur during free radical oxidative damage. In this study, leucine-enkephalin-glycerophosphatidylcholine alka(e)nal adducts were analyzed by electrospray tandem mass spectrometry (MS/MS). Upon collision-induced dissociation of the Leucine enkephalin-2-(9-oxo-nonanoyl)-1-palmitoyl-3-glycerophosphatidylcholine, an alkanal Schiff adduct observed at m/z 1187.7, the main product ions were attributed to the phosphocholine polar head and loss of the peptide. Also, product ions resulting from characteristic losses of phosphatidylcholines and cleavages of the peptide chain (mainly b-type) were observed. Additional product ions formed by combined peptide and phosphatidylcholine fragmentations were identified. The fragmentation pattern of the leucine enkephalin-alkanal Schiff adduct and the leucine enkephalin-alkenal phosphatidylcholine Schiff and Michael adducts were similar, although the loss of the peptide for the Michael adduct should occur through a distinct mechanism. These fragmentation pathways differ greatly from those described for peptide-lipid Schiff and Michael adducts, in which only peptide chai...Continue Reading

References

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Jan 8, 1999·Journal of the American Society for Mass Spectrometry·C Cheng, M L Gross
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Citations

Jun 19, 2013·Journal of Proteomics·Rosário M DominguesCorinne M Spickett
Aug 2, 2008·Chemistry and Physics of Lipids·M Rosário M DominguesPedro Domingues
Mar 12, 2009·Biomedical Chromatography : BMC·M Rosário M DominguesPedro Domingues
Mar 25, 2015·Journal of Mass Spectrometry : JMS·Ivana MilicMaria Fedorova
Jun 2, 2007·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Ana ReisP Domingues
Dec 5, 2015·Journal of Mass Spectrometry : JMS·Ivana MilicMaria Fedorova
Jan 31, 2007·Journal of Mass Spectrometry : JMS
May 8, 2021·Biochemical Society Transactions·Ahilanandan Dushianthan, Anthony Postle

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