Reaction participants Show >> << Hide
- Name help_outline 1-(1,2-saturated alkyl)-2-acyl-sn-glycero-3-phosphoethanolamine Identifier CHEBI:75028 Charge 0 Formula C8H16NO7PR2 SMILEShelp_outline [NH3+]CCOP([O-])(=O)OC[C@@H](COCC[*])OC([*])=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
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Namehelp_outline
Fe(II)-[cytochrome b5]
Identifier
RHEA-COMP:10438
Reactive part
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- Name help_outline Fe2+ Identifier CHEBI:29033 (CAS: 15438-31-0) help_outline Charge 2 Formula Fe InChIKeyhelp_outline CWYNVVGOOAEACU-UHFFFAOYSA-N SMILEShelp_outline [Fe++] 2D coordinates Mol file for the small molecule Search links Involved in 263 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 9,431 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline O2 Identifier CHEBI:15379 (CAS: 7782-44-7) help_outline Charge 0 Formula O2 InChIKeyhelp_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILEShelp_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,709 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- 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 29 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
Fe(III)-[cytochrome b5]
Identifier
RHEA-COMP:10439
Reactive part
help_outline
- Name help_outline Fe3+ Identifier CHEBI:29034 (CAS: 20074-52-6) help_outline Charge 3 Formula Fe InChIKeyhelp_outline VTLYFUHAOXGGBS-UHFFFAOYSA-N SMILEShelp_outline [Fe+3] 2D coordinates Mol file for the small molecule Search links Involved in 248 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H2O Identifier CHEBI:15377 (Beilstein: 3587155; CAS: 7732-18-5) help_outline Charge 0 Formula H2O InChIKeyhelp_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILEShelp_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,204 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:22956 | RHEA:22957 | RHEA:22958 | RHEA:22959 | |
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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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Studies on the biosynthesis of plasmalogens. Precursors in the biosynthesis of plasmalogens: on the stereospecificity of the biochemical dehydrogenation of the 1-O-alkyl glyceryl to the 1-O-alk-1'-enyl glyceryl ether bond.
Stoffel W., LeKim D.
Hoppe Seylers Z Physiol Chem 352:501-511(1971) [PubMed] [EuropePMC]
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A bacterial light response reveals an orphan desaturase for human plasmalogen synthesis.
Gallego-Garcia A., Monera-Girona A.J., Pajares-Martinez E., Bastida-Martinez E., Perez-Castano R., Iniesta A.A., Fontes M., Padmanabhan S., Elias-Arnanz M.
Plasmalogens are glycerophospholipids with a hallmark <i>sn</i>-1 vinyl ether bond. These lipids are found in animals and some bacteria and have proposed membrane organization, signaling, and antioxidant roles. We discovered the plasmanylethanolamine desaturase activity that is essential for vinyl ... >> More
Plasmalogens are glycerophospholipids with a hallmark <i>sn</i>-1 vinyl ether bond. These lipids are found in animals and some bacteria and have proposed membrane organization, signaling, and antioxidant roles. We discovered the plasmanylethanolamine desaturase activity that is essential for vinyl ether bond formation in a bacterial enzyme, CarF, which is a homolog of the human enzyme TMEM189. CarF mediates light-induced carotenogenesis in <i>Myxococcus xanthus</i>, and plasmalogens participate in sensing photooxidative stress through singlet oxygen. TMEM189 and other animal homologs could functionally replace CarF in <i>M. xanthus</i>, and knockout of TMEM189 in a human cell line eliminated plasmalogens. Discovery of the human plasmanylethanolamine desaturase will spur further study of plasmalogen biogenesis, functions, and roles in disease. << Less
Science 366:128-132(2019) [PubMed] [EuropePMC]
This publication is cited by 5 other entries.
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The biosynthesis of plasmalogens by rat brain: involvement of the microsomal electron transport system.
Wykle R.L., Schremmer Lockmiller J.M.
The biosynthesis of 1-alk-1'-enyl-2-acyl-sn-glycero-3-phosphoethanolamine (ethanolamine plasmalogens) was studied using 1-[1-14C]hexadecyl-sn-glycero-3-phosphoethanolamine as the substrate and EDTA-washed microsomes from brains of 14-day-old rats. It was found that the 1-E11-14C]hexadecyl-sn-glyce ... >> More
The biosynthesis of 1-alk-1'-enyl-2-acyl-sn-glycero-3-phosphoethanolamine (ethanolamine plasmalogens) was studied using 1-[1-14C]hexadecyl-sn-glycero-3-phosphoethanolamine as the substrate and EDTA-washed microsomes from brains of 14-day-old rats. It was found that the 1-E11-14C]hexadecyl-sn-glycero-3-phosphoethanolamine was first acylated to form 1-[1-14C]hexadecyl-2-acyl-sn-glycero-3-phosphoethanolamine, then was desaturated to form 1-[1-14C]hexadec-1'-enyl-2-acyl-sn-glycero-3-phosphoethanolamine. The desaturation required O2 and NADH or NADPH and was inhibited by KCN but not by CO. The data indicated that the desaturation is carried out by a mixed-function oxidase system similar to that involved in the desaturation of fatty acids and that the pathway for the biosynthesis of plasmalogens in brain is similar to that previously found in other tissues. The desaturase was not stimulated by ATP and Mg2plus nor inhibited by EDTA. The specific activity of microsomes from brains of rats of different ages was determined; the activity decreased with age until in adults the activity was only 15% that of the 12--14-day-old rats. << Less
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Enzymatic synthesis of plasmalogens. Characterization of the 1-O-alkyl-2-acyl-8n-glycero-3-phosphorylethanolamine desaturase from mucosa of hamster small intestine.
Paltauf F., Holasek A.
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Evidence for a mixed function oxidase in the biosynthesis of ethanolamine plasmalogens from 1-alkyl-2-acyl-sn-glycero-3-phosphorylethanolamine.
Wykle R.L., Blank M.L., Malone B., Snyder F.
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Evidence for the participation of cytochrome b5 in plasmalogen biosynthesis.
Paltuaf F., Prough R.A., Masters B.S., Johnston J.M.