Tandem mass spectrometry of negative ions from choline phospholipid molecular species related to platelet activating factor
| Autor: | J. A. Zirrolli, K. L. Clay, R. C. Murphy |
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| Rok vydání: | 1991 |
| Předmět: |
Molecular Structure
Stereochemistry Organic Chemistry Molecular Conformation Substituent Phospholipid Phospholipid Ethers Ether Cell Biology Spectrometry Mass Fast Atom Bombardment Fast atom bombardment Tandem mass spectrometry Mass spectrometry Biochemistry Structure-Activity Relationship chemistry.chemical_compound chemistry Choline Organic chemistry lipids (amino acids peptides and proteins) Carboxylate Platelet Activating Factor |
| Zdroj: | Lipids. 26:1112-1116 |
| ISSN: | 1558-9307 0024-4201 |
| DOI: | 10.1007/bf02536512 |
| Popis: | Fast atom bombardment mass spectrometry of choline phospholipids produces negative ions characteristic of the intact molecule and tandem mass spectrometry of collision-induced decomposition of M-15 anions characterizes both the identity and substituent position of radyl groups. Certain choline phospholipid molecular species which may be of special interest in the generation of platelet activating factor contain a highly unsaturated fatty acyl substituent at sn-2 and an ether radyl group at sn-1; other choline phospholipid molecular species which contain esterified arachidonic acid are of interest as potential sources of arachidonate for eicosanoid biosynthesis. Collisional activated decomposition of 1-hexadecanoyl-2-arachidonoyl-sn-glycero-phosphocholine produce abundant carboxylate anions at m/z 303 (arachidonate) and m/z 255 (hexadecanoate) in a ratio of 3:1, diagnostic for the sn-2 arachidonoyl position. The ether analog, 1-O-hexadecyl-2-arachidonoyl glycerophosphocholine, produces only one collision-induced dissociation ion at m/z 303 and no product ions corresponding to the ether substituent at sn-1. Molecular weight information from the M-15 ion combined with the CID generated carboxylate anions completely characterize these important phospholipids. Precursor ion studies of M-15 anions from glycero-phosphocholine lipids indicate that this ion is derived directly from a unique adduct ion formed by attachment of the molecular species to a matrix alkoxide ion, neutralizing the positive charge of the quaternary choline nitrogen. Decomposition of this adduct ion yields a methylated matrix molecule and the nominal M-15 ion. |
| Databáze: | OpenAIRE |
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