Enzymes
| UniProtKB help_outline | 2,791 proteins |
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- Name help_outline (9Z,12Z)-octadecadienoate Identifier CHEBI:30245 (Beilstein: 4139597; CAS: 1509-85-9) help_outline Charge -1 Formula C18H31O2 InChIKeyhelp_outline OYHQOLUKZRVURQ-HZJYTTRNSA-M SMILEShelp_outline CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 52 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline AH2 Identifier CHEBI:17499 Charge 0 Formula RH2 SMILEShelp_outline *([H])[H] 2D coordinates Mol file for the small molecule Search links Involved in 2,713 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 (13R)-hydroxy-(9Z,11E)-octadecadienoate Identifier CHEBI:136655 Charge -1 Formula C18H31O3 InChIKeyhelp_outline HNICUWMFWZBIFP-PIHGWCCBSA-M SMILEShelp_outline C(CCCCCCC\C=C/C=C/[C@@H](CCCCC)O)(=O)[O-] 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline A Identifier CHEBI:13193 Charge Formula R SMILEShelp_outline * 2D coordinates Mol file for the small molecule Search links Involved in 2,783 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:75455 | RHEA:75456 | RHEA:75457 | RHEA:75458 | |
|---|---|---|---|---|
| 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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Stereochemistry of oxygenation of linoleic acid catalyzed by prostaglandin-endoperoxide H synthase-2.
Hamberg M.
Linoleic acid was incubated with prostaglandin-endoperoxide H synthase-2 (PGHS-2) from ovine placenta. A product consisting of regio- and stereoisomeric hydroxyoctadecadienoic (HOD) acids was obtained. Analysis by straight-phase high-performance liquid chromatography followed by chiral-phase high- ... >> More
Linoleic acid was incubated with prostaglandin-endoperoxide H synthase-2 (PGHS-2) from ovine placenta. A product consisting of regio- and stereoisomeric hydroxyoctadecadienoic (HOD) acids was obtained. Analysis by straight-phase high-performance liquid chromatography followed by chiral-phase high-performance liquid chromatography demonstrated that linoleic acid was preferentially oxygenated at C-9 to produce the following mixture of HODs: 9(R)-HOD (52%), 9(S)-HOD (11%), 13(R)-HOD (2%), and 13(S)-HOD (35%). As a comparison, linoleic acid was incubated with microsomal prostaglandin-endoperoxide H synthase-1 (PGHS-1) from ovine vesicular gland. This resulted in a product having the following composition: 9(R)-HOD (73%), 9(S)-HOD (9%), 13(R)-HOD (1%), and 13(S)-HOD (17%). The stereochemistry of the hydrogen which was removed from C-11 during the conversion of linoleic acid into hydroxy acids in the presence of PGHS-1 or PGHS-2 was determined by incubation of [(11R)-2H]- and [(11S)-2H]linoleic acids followed by mass spectrometric analysis of the isotope contents of the individual hydroxy acid isomers. Both enzymes were found to catalyze oxygenations which involved stereospecific removal of the (11S) hydrogen and retention of the (11R) hydrogen. The major hydroxy acids, i.e., 9(R)-HOD and 13(S)-HOD, were formed from linoleic acid in reactions which involved antarafacial hydrogen abstraction and oxygen insertion. It is concluded that the initial steps of the PGHS-2- and PGHS-1-catalyzed oxygenations proceed with identical stereochemistry and involve stereospecific removal of the pro-S hydrogen from the omega 8-methylene group of the substrate. << Less
Arch. Biochem. Biophys. 349:376-380(1998) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.