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- Name help_outline 1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphoethanolamine Identifier CHEBI:77290 Charge 0 Formula C8H14NO7PR2 SMILEShelp_outline [NH3+]CCOP([O-])(=O)OC[C@@H](CO\C=C/[*])OC([*])=O 2D coordinates Mol file for the small molecule Search links Involved in 27 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline a 1,2-diacyl-sn-glycero-3-phosphocholine Identifier CHEBI:57643 Charge 0 Formula C10H18NO8PR2 SMILEShelp_outline [C@](COC(=O)*)(OC(=O)*)([H])COP(OCC[N+](C)(C)C)([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 315 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline a 2-acyl-sn-glycero-3-phosphocholine Identifier CHEBI:57875 Charge 0 Formula C9H19NO7PR 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 97 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline N-acyl-1-O-(1Z-alkenyl)-2-acyl-sn-glycero-3-phosphoethanolamine Identifier CHEBI:140451 Charge -1 Formula C9H12NO8PR3 SMILEShelp_outline C(*)(=O)O[C@@H](COP(=O)(OCCNC(*)=O)[O-])CO/C=C\* 2D coordinates Mol file for the small molecule Search links Involved in 5 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:63596 | RHEA:63597 | RHEA:63598 | RHEA:63599 | |
|---|---|---|---|---|
| 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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Phosphatidylserine-stimulated production of N-acyl-phosphatidylethanolamines by Ca2+-dependent N-acyltransferase.
Hussain Z., Uyama T., Kawai K., Binte Mustafiz S.S., Tsuboi K., Araki N., Ueda N.
N-acyl-phosphatidylethanolamine (NAPE) is known to be a precursor for various bioactive N-acylethanolamines including the endocannabinoid anandamide. NAPE is produced in mammals through the transfer of an acyl chain from certain glycerophospholipids to phosphatidylethanolamine (PE) by Ca<sup>2+</s ... >> More
N-acyl-phosphatidylethanolamine (NAPE) is known to be a precursor for various bioactive N-acylethanolamines including the endocannabinoid anandamide. NAPE is produced in mammals through the transfer of an acyl chain from certain glycerophospholipids to phosphatidylethanolamine (PE) by Ca<sup>2+</sup>-dependent or -independent N-acyltransferases. The ε isoform of mouse cytosolic phospholipase A<sub>2</sub> (cPLA<sub>2</sub>ε) was recently identified as a Ca<sup>2+</sup>-dependent N-acyltransferase (Ca-NAT). In the present study, we first showed that two isoforms of human cPLA<sub>2</sub>ε function as Ca-NAT. We next purified both mouse recombinant cPLA<sub>2</sub>ε and its two human orthologues to examine their catalytic properties. The enzyme absolutely required Ca<sup>2+</sup> for its activity and the activity was enhanced by phosphatidylserine (PS). PS enhanced the activity 25-fold in the presence of 1 mM CaCl<sub>2</sub> and lowered the EC<sub>50</sub> value of Ca<sup>2+</sup> >8-fold. Using a PS probe, we showed that cPLA<sub>2</sub>ε largely co-localizes with PS in plasma membrane and organelles involved in the endocytic pathway, further supporting the interaction of cPLA<sub>2</sub>ε with PS in living cells. Finally, we found that the Ca<sup>2+</sup>-ionophore ionomycin increased [<sup>14</sup>C]NAPE levels >10-fold in [<sup>14</sup>C]ethanolamine-labeled cPLA<sub>2</sub>ε-expressing cells while phospholipase A/acyltransferase-1, acting as a Ca<sup>2+</sup>-independent N-acyltransferase, was insensitive to ionomycin for full activity. In conclusion, PS potently stimulated the Ca<sup>2+</sup>-dependent activity and human cPLA<sub>2</sub>ε isoforms also functioned as Ca-NAT. << Less
Biochim. Biophys. Acta 1863:493-502(2018) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.