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- Name help_outline 1ʼ-[1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phospho]-3ʼ-[1-(9Z-octadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phospho]-glycerol Identifier CHEBI:173223 Charge -2 Formula C81H146O17P2 InChIKeyhelp_outline HGIKPGJCIWRORL-TVFZIFOYSA-L SMILEShelp_outline [C@H](OC(CCCCCCC/C=C\CCCCCCCC)=O)(COP(OCC(COP(OC[C@H](OC(=O)CCCCCCC/C=C\C/C=C\CCCCC)COC(CCCCCCC/C=C\CCCCCCCC)=O)([O-])=O)O)([O-])=O)COC(CCCCCCC/C=C\CCCCCCCC)=O 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 1-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine Identifier CHEBI:28733 Charge 0 Formula C26H50NO7P InChIKeyhelp_outline SPJFYYJXNPEZDW-FTJOPAKQSA-N SMILEShelp_outline CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C 2D coordinates Mol file for the small molecule Search links Involved in 7 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1,2-di-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Identifier CHEBI:42027 (CAS: 998-06-1) help_outline Charge 0 Formula C44H80NO8P InChIKeyhelp_outline FVXDQWZBHIXIEJ-LNDKUQBDSA-N SMILEShelp_outline CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC 2D coordinates Mol file for the small molecule Search links Involved in 7 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1ʼ-[1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phospho]-3ʼ-[1-(9Z-octadecenoyl)-sn-glycero-3-phospho]-glycerol Identifier CHEBI:77259 Charge -2 Formula C63H116O16P2 InChIKeyhelp_outline NGKFXJNJRVPYMN-IYJDKBLTSA-L SMILEShelp_outline CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC(O)COP([O-])(=O)OC[C@@H](COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC 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
Cross-references
| RHEA:67768 | RHEA:67769 | RHEA:67770 | RHEA:67771 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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More general form(s) of this reaction
Publications
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Role of Acyl Chain Composition of Phosphatidylcholine in Tafazzin-Mediated Remodeling of Cardiolipin in Liposomes.
Abe M., Sawada Y., Uno S., Chigasaki S., Oku M., Sakai Y., Miyoshi H.
Remodeling of the acyl chain compositions of cardiolipin (CL) species by the transacylase tafazzin is an important process for maintaining optimal mitochondrial functions. The results of mechanistic studies on the tafazzin-mediated transacylation from phosphatidylcholine (PC) to monolyso-CL (MLCL) ... >> More
Remodeling of the acyl chain compositions of cardiolipin (CL) species by the transacylase tafazzin is an important process for maintaining optimal mitochondrial functions. The results of mechanistic studies on the tafazzin-mediated transacylation from phosphatidylcholine (PC) to monolyso-CL (MLCL) in artificial lipid membranes are controversial. The present study investigated the role of the acyl chain composition of PC in the Saccharomyces cerevisiae tafazzin-mediated remodeling of CL by examining the structural factors responsible for the superior acyl donor ability of dipalmitoleoyl (16:1) PC over dipalmitoyl (16:0) PC. To this end, we synthesized systematic derivatives of dipalmitoleoyl PC; for example, the location of the cis double bond was migrated from the Δ9-position toward either end of the acyl chains (the Δ5- or Δ13-position), the cis double bond in the sn-1 or sn-2 position or both, was changed to a trans form, and palmitoleoyl and palmitoyl groups were exchanged in the sn-1 and sn-2 positions, maintaining similar PC fluidities. Analyses of the tafazzin-mediated transacylation from these PCs to sn-2'-MLCL(18:1-18:1/18:1-OH) in the liposomal membrane revealed that tafazzin strictly discriminates the molecular configuration of the acyl chains of PCs, including their glycerol positions (sn-1 or sn-2); however, the effects of PC fluidity on the reaction may not be neglected. On the basis of the findings described herein, we discuss the relevance of the so-called thermodynamic remodeling hypothesis that presumes no acyl selectivity of tafazzin. << Less
Biochemistry 56:6268-6280(2017) [PubMed] [EuropePMC]
This publication is cited by 7 other entries.