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- Name help_outline 1-O-alkyl-2-acyl-sn-glycero-3-phosphocholine Identifier CHEBI:36702 Charge 0 Formula C9H18NO7PR2 SMILEShelp_outline C[N+](C)(C)CCOP([O-])(=O)OC[C@@H](CO[*])OC([*])=O 2D coordinates Mol file for the small molecule Search links Involved in 42 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1-O-alkyl-sn-glycero-3-phosphoethanolamine Identifier CHEBI:76168 Charge 0 Formula C5H13NO6PR SMILEShelp_outline [NH3+]CCOP([O-])(=O)OC[C@H](O)CO[*] 2D coordinates Mol file for the small molecule Search links Involved in 4 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1-O-alkyl-2-acyl-sn-glycero-3-phosphoethanolamine Identifier CHEBI:60520 Charge 0 Formula C6H12NO7PR2 SMILEShelp_outline P(OC[C@@H](CO*)OC(=O)*)(=O)(OCC[NH3+])[O-] 2D coordinates Mol file for the small molecule Search links Involved in 10 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1-O-alkyl-sn-glycero-3-phosphocholine Identifier CHEBI:30909 Charge 0 Formula C8H19NO6PR SMILEShelp_outline C[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO[*] 2D coordinates Mol file for the small molecule Search links Involved in 42 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:20972 | RHEA:20973 | RHEA:20974 | RHEA:20975 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Related reactions help_outline
Specific form(s) of this reaction
Publications
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Transfer of arachidonic acid between phospholipids in rat liver microsomes.
Irvine R.F., Dawson R.M.
Biochem Biophys Res Commun 91:1399-1405(1979) [PubMed] [EuropePMC]
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Acylation of lysophospholipids by rabbit alveolar macrophages. Specificities of CoA-dependent and CoA-independent reactions.
Robinson M., Blank M.L., Snyder F.
Intact alveolar macrophages were found to acylate alkyl- and acyllysophospholipids with a high selectivity for arachidonate. A specific mechanism appears responsible for the incorporation of arachidonate into lysophospholipids in intact cells since the kinetic pattern for the formation of the 20:4 ... >> More
Intact alveolar macrophages were found to acylate alkyl- and acyllysophospholipids with a high selectivity for arachidonate. A specific mechanism appears responsible for the incorporation of arachidonate into lysophospholipids in intact cells since the kinetic pattern for the formation of the 20:4 species was different from all other species. This specificity was investigated in more detail by examining the enzymatic acylation of 1-alkyl-2-lyso-sn-glycero-3-phosphocholine by macrophage membranes; in the absence of CoA, ATP, and Mg2+, this lysophospholipid was acylated with a high preference for arachidonate that was independent of added free fatty acids. The addition of CoA alone increased the rate of acylation of 1-alkyl-2-lyso-sn-glycero-3-phosphocholine, mainly due to an increase in the formation of species other than those containing arachidonate. When CoA, ATP, and Mg2+ were present, the macrophage membranes catalyzed the acylation of 1-alkyl-2-lyso-sn-glycero-3-phosphocholine without preference for arachidonate. A different apparent Km and Vmax was observed for reactions involving each cofactor condition. We conclude that the acylation of alkyl- and acyllysophospholipids by rabbit alveolar macrophages occurs by three separate mechanisms: a CoA-independent transacylation, a CoA-dependent transacylation (reverse reaction catalyzed by acyl-CoA acyltransferase), and an acyl-CoA-dependent acylation. The CoA-independent transacylation reaction is unique in that it is specific for arachidonate and accounts for the selective acylation of alkyl- and acyllysophospholipids by arachidonate in membrane preparations of alveolar macrophages. This reaction appears to be extremely important in the remodeling of phospholipid molecular species and the mobilization of arachidonate into ether-linked lipids. The transfer of arachidonate to 1-alkyl-2-lyso-sn-glycero-3-phosphocholine also is of importance in the final inactivation step for platelet activating factor (1-alkyl-2-acetyl-sn-glycero-3-phosphocholine), whereby 1-alkyl-2-arachidonoyl-sn-glycerol-3-phosphocholine (a stored precursor of both platelet activating factor and arachidonic acid metabolites) is formed. << Less
J Biol Chem 260:7889-7895(1985) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.
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The role of transacylases in the metabolism of arachidonate and platelet activating factor.
Snyder F., Lee T.C., Blank M.L.
Prog Lipid Res 31:65-86(1992) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.