Reaction participants Show >> << Hide
- Name help_outline 1-acyl-2-(9Z,12Z)-octadecadienoyl-sn-glycero-3-phosphocholine Identifier CHEBI:60000 Charge 0 Formula C27H49NO8PR SMILEShelp_outline CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H](COC([*])=O)COP([O-])(=O)OCC[N+](C)(C)C 2D coordinates Mol file for the small molecule Search links Involved in 22 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
help_outline
- 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 250 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 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 2,648 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 1-acyl-2-(9Z,12Z,15Z-octadecatrienoyl)-sn-glycero-3-phosphocholine Identifier CHEBI:167146 Charge 0 Formula C27H47NO8PR SMILEShelp_outline C(C[N+](C)(C)C)OP(=O)([O-])OC[C@H](OC(CCCCCCC/C=C\C/C=C\C/C=C\CC)=O)COC(=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(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 234 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 6,048 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:66504 | RHEA:66505 | RHEA:66506 | RHEA:66507 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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A novel fungal omega3-desaturase with wide substrate specificity from arachidonic acid-producing Mortierella alpina 1S-4.
Sakuradani E., Abe T., Iguchi K., Shimizu S.
A filamentous fungus, Mortierella alpina 1S-4, is capable of producing not only arachidonic acid (AA; 20:4n-6) but also eicosapentaenoic acid (EPA; 20:5n-3) below a cultural temperature of 20 degrees C. Here, we describe the isolation and characterization of a gene (maw3) that encodes a novel omeg ... >> More
A filamentous fungus, Mortierella alpina 1S-4, is capable of producing not only arachidonic acid (AA; 20:4n-6) but also eicosapentaenoic acid (EPA; 20:5n-3) below a cultural temperature of 20 degrees C. Here, we describe the isolation and characterization of a gene (maw3) that encodes a novel omega3-desaturase from M. alpina 1S-4. Based on the conserved sequence information for M. alpina 1S-4 Delta12-desaturase and Saccharomyces kluyveri omega3-desaturase, the omega3-desaturase gene from M. alpina 1S-4 was cloned. Homology analysis of protein databases revealed that the amino acid sequence showed 51% identity, at the highest, with M. alpina 1S-4 Delta12-desaturase, whereas it exhibited 36% identity with Sac. kluyveri omega3-desaturase. The cloned cDNA was confirmed to encode the omega3-desaturase by its expression in the yeast Sac. cerevisiae. Analysis of the fatty acid composition of the yeast transformant demonstrated that 18-carbon and 20-carbon n-3 polyunsaturated fatty acids (PUFAs) were accumulated through conversion of exogenous 18-carbon and 20-carbon n-6 PUFAs. The substrate specificity of the M. alpina 1S-4 omega3-desaturase differs from those of the known fungal omega3-desaturases from Sac. kluyveri and Saprolegnia diclina. Plant, cyanobacterial and Sac. kluyveri omega3-desaturases desaturate 18-carbon n-6 PUFAs, Spr. diclina omega3-desaturase desaturates 20-carbon n-6 PUFAs and Caenorhabditis elegans omega3-desaturase prefers 18-carbon n-6 PUFAs as substrates rather than 20-carbon n-6 PUFAs. The substrate specificity of M. alpina 1S-4 omega3-desaturase is rather similar to that of C. elegans omega3-desaturase, but the M. alpina omega3-desaturase can more effectively convert AA into EPA when expressed in yeast. The M. alpina 1S-4 omega3-desaturase is the first known fungal desaturase that uses both 18-carbon and 20-carbon n-6 PUFAs as substrates. << Less
Appl. Microbiol. Biotechnol. 66:648-654(2005) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.
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Mutants of Arabidopsis deficient in the synthesis of alpha-linolenate. Biochemical and genetic characterization of the endoplasmic reticulum linoleoyl desaturase.
Browse J., McConn M., James D. Jr., Miquel M.
The overall fatty compositions of leaf and root lipids from a mutant of Arabidopsis thaliana were characterized by reduced levels of linolenate (18:3) and correspondingly elevated levels of linoleate (18:2) as a consequence of a single nuclear mutation at the fad3 locus. Comparison of the fatty ac ... >> More
The overall fatty compositions of leaf and root lipids from a mutant of Arabidopsis thaliana were characterized by reduced levels of linolenate (18:3) and correspondingly elevated levels of linoleate (18:2) as a consequence of a single nuclear mutation at the fad3 locus. Comparison of the fatty acid compositions of individual lipids from wild type and mutant plants showed that chloroplast lipids were largely unaffected by the mutation, whereas each of the phospholipids synthesized on the endoplasmic reticulum in the mutant exhibited a marked reduction in the proportion of 18:3 relative to wild type. These and other results indicate that the fad3 mutants are deficient in the activity of an endoplasmic reticulum 18:2 desaturase. In root tissues, this enzyme appears to account for over 80% of the 18:3 present. However, in young leaves of the mutant, phosphatidylcholine (the major phospholipid) contains 16% 18:3 compared with 29% in the wild type, and the proportion of 18:3 in this lipid increases with plant age in both wild type and mutant plants. These results reflect an exchange of lipid between the chloroplast and endoplasmic reticulum that allows the chloroplast desaturases to provide highly unsaturated lipids to the extrachloroplast membranes of leaf cells. << Less
J. Biol. Chem. 268:16345-16351(1993) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.