ArticleJournal of the American Society for Mass Spectrometry2006
Sources of artefacts in the electrospray ionization mass spectra of saturated diacylglycerophosphocholines: from condensed phase hydrolysis reactions through to gas phase intercluster reactions.
Article in Journal of the American Society for Mass Spectrometry, 2006. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 34 citations in OpenAlex.
- Comprehensive and Reproducible Untargeted Lipidomic Workflow Using LC-QTOF Validated for Human Plasma Analysis.Journal of proteome research · 2018Article
- Vesicular Delivery of the Antifungal Antibiotics of Lysobacter enzymogenes C3.Applied and environmental microbiology · 2018Article
- Ambient Molecular Analysis of Biological Tissue Using Low-Energy, Femtosecond Laser Vaporization and Nanospray Postionization Mass Spectrometry.Journal of the American Society for Mass Spectrometry · 2016Article
- Structural identities of four glycosylated lipids in the oral bacterium Streptococcus mutans UA159.Biochimica et biophysica acta · 2012Article
- Competition between covalent and noncovalent bond cleavages in dissociation of phosphopeptide-amine complexes.Physical chemistry chemical physics : PCCP · 2011Article
- Aromatic residues in the C-terminal helix of human apoC-I mediate phospholipid interactions and particle morphology.Journal of lipid research · 2009Article
- Electron capture dissociation of complexes of diacylglycerophosphocholine and divalent metal ions: competition between charge reduction and radical induced phospholipid fragmentation.Journal of the American Society for Mass Spectrometry · 2008Article
- Resolvin D1, protectin D1, and related docosahexaenoic acid-derived products: Analysis via electrospray/low energy tandem mass spectrometry based on spectra and fragmentation mechanisms.Journal of the American Society for Mass Spectrometry · 2007Article
- Current literature in mass spectrometry.Journal of mass spectrometry : JMS · 2007Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The mass spectra of diacylglycerophosphocholine phospholipids comprised of saturated fatty acids (1,2-dipentanoyl-sn-glycero-3-phosphocholine (D5PC); 1,2-dihexanoyl-sn-glycero-3-phosphocholine (D6PC), and 1,2-dimyristoyl-sn-glycero-3-phosphocholine (D14PC)) are sensitive to the electrospray ionization (ESI) conditions. When fresh solutions of phospholipid in 10 mM ammonium acetate are subjected to ESI, protonated oligomeric clusters, [DxPCn + H]+ (x = 5, 6, and 14) are observed in the following different types of mass spectrometers: 3D-quadrupole ion trap; linear ion trap, and triple quadrupole. The formation of the protonated cluster ions is not unique to the ion trap instruments, although they tend to be more abundant in these instruments. As the ESI solutions age, new ions are observed, which correspond to acid-catalyzed solution phase deacylation reactions. The collision induced dissociation fragmentation reactions of the oligomer cluster ions exhibit a distinct dependence on the cluster size, with the larger clusters (n > 2) simply fragmenting via the loss of lipid monomers. In contrast, the fragmentation of the dimeric cluster ion is unique, resulting in a number of additional reactions including covalent bond formation via intermolecular cluster SN2 reactions and SN2 transfer of a methyl group. The nature of the charge has a significant role in the formation of products via these intermolecular cluster reactions. Changing the head group to phosphoethanolamine "switches off" the SN2 reactions, while changing the cation from a proton to either a sodium or a potassium ion, diminishes the intermolecular reactions relative to monomer loss. Semi empirical PM3 calculations on [D6PC2 + H]+ suggest that the SN2 reactions are thermodynamically favored over simple monomer loss. These results have important implications in the field of lipidomics.
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