Reaction participants Show >> << Hide
- Name help_outline 1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine Identifier CHEBI:74669 (CAS: 4235-95-4) help_outline Charge 0 Formula C44H84NO8P InChIKeyhelp_outline SNKAWJBJQDLSFF-NVKMUCNASA-N SMILEShelp_outline CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC 2D coordinates Mol file for the small molecule Search links Involved in 29 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1-O-hexadecyl-2-O-methyl-sn-glycerol Identifier CHEBI:76063 Charge 0 Formula C20H42O3 InChIKeyhelp_outline XAWCMDFDFNRKGK-FQEVSTJZSA-N SMILEShelp_outline CCCCCCCCCCCCCCCCOC[C@H](CO)OC 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (9Z-octadecenoyl)-sn-glycero-3-phosphocholine Identifier CHEBI:76083 Charge 0 Formula C26H52NO7P SMILEShelp_outline C[N+](C)(C)CCOP([O-])(=O)OC[C@@H](CO[*])O[*] 2D coordinates Mol file for the small molecule Search links Involved in 51 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1-O-hexadecyl-2-O-methyl-3-(9Z)-octadecenoyl-sn-glycerol Identifier CHEBI:76064 Charge 0 Formula C38H74O4 InChIKeyhelp_outline CEVZNCTVUSCKBM-XZRWTQCASA-N SMILEShelp_outline CCCCCCCCCCCCCCCCOC[C@H](COC(=O)CCCCCCC\C=C/CCCCCCCC)OC 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:38723 | RHEA:38724 | RHEA:38725 | RHEA:38726 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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The acylation of lipophilic alcohols by lysosomal phospholipase A2.
Abe A., Hiraoka M., Shayman J.A.
A novel lysosomal phospholipase A(2) (LPLA2) with specificity toward phosphatidylethanolamine and phosphatidylcholine was previously purified and cloned. LPLA2 transfers sn-1 or sn-2 acyl groups of phospholipids to the C1 hydroxyl of the short-chain ceramide N-acetylsphingosine (NAS) under acidic ... >> More
A novel lysosomal phospholipase A(2) (LPLA2) with specificity toward phosphatidylethanolamine and phosphatidylcholine was previously purified and cloned. LPLA2 transfers sn-1 or sn-2 acyl groups of phospholipids to the C1 hydroxyl of the short-chain ceramide N-acetylsphingosine (NAS) under acidic conditions. The common features of lipophilic alcohols serving as acceptor molecules in the transacylase reaction were examined. 1-O-Hexadecyl-2-acetyl-sn-glycerol (HAG) was acylated by LPLA2 similar to NAS. HAG competed with NAS and inhibited NAS acylation. The transacylation of 1-O-hexadecyl-glycerol (HG), 1-O-palmityl-2-O-methyl-sn-glycerol (PMG), and monoacylglycerols was also investigated. HG, PMG, 1- or 3-palmitoyl-sn-glycerol, and 2-palmitoylglycerol were converted to 1,3-alkylacylglycerol, 1,2-dialkyl-3-acylglycerol, 1,3-diacylglycerol, and 1,2- or 2,3-diacylglycerol, respectively. HG and monoacylglycerol inhibited the acylation of NAS by the enzyme with IC(50) values of 35 and 45 microM, respectively. Additionally, the enzyme acylated glycerol to produce 1- or 3-acyl-sn-glycerol but not 2-acylglycerol. Therefore, the preferred acceptor molecules for LPLA2 are primary alcohols with one long carbon chain and one small nonpolar residue linked to the C2 position of ethanol. The enzyme acylated other natural lipophilic alcohols, including anandamide and oleoylethanolamide. Thus, LPLA2 may function to remodel acyl groups and modulate the biological and pharmacological activities of some lipophilic alcohols. << Less
J. Lipid Res. 48:2255-2263(2007) [PubMed] [EuropePMC]
This publication is cited by 36 other entries.