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- Name help_outline tetradecanedioyl-CoA Identifier CHEBI:77084 Charge -5 Formula C35H55N7O19P3S InChIKeyhelp_outline TVXJIGZINAEEEG-XIOMLZLPSA-I SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCC([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 3 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 2,727 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (2E)-tetradecenedioyl-CoA Identifier CHEBI:77039 Charge -5 Formula C35H53N7O19P3S InChIKeyhelp_outline SFSYDKBWVPWWFQ-KHXGTSCESA-I SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)\C=C\CCCCCCCCCCC([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 H2O2 Identifier CHEBI:16240 (CAS: 7722-84-1) help_outline Charge 0 Formula H2O2 InChIKeyhelp_outline MHAJPDPJQMAIIY-UHFFFAOYSA-N SMILEShelp_outline [H]OO[H] 2D coordinates Mol file for the small molecule Search links Involved in 452 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:40271 | RHEA:40272 | RHEA:40273 | RHEA:40274 | |
|---|---|---|---|---|
| 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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Rat liver metabolism of dicarboxylic acids.
Vamecq J., Draye J.P., Brison J.
Recently, we demonstrated in rat liver that dicarboxylic acids containing more than five carbons can be activated by a microsomal dicarboxylyl-CoA synthetase (J. Vamecq, E. de Hoffmann, and F. Van Hoof. Biochem. J. 230: 683-693, 1985). The products of this reaction, dicarboxylyl-CoA esters, were f ... >> More
Recently, we demonstrated in rat liver that dicarboxylic acids containing more than five carbons can be activated by a microsomal dicarboxylyl-CoA synthetase (J. Vamecq, E. de Hoffmann, and F. Van Hoof. Biochem. J. 230: 683-693, 1985). The products of this reaction, dicarboxylyl-CoA esters, were found to be substrates for an H2O2-generating dicarboxylyl-CoA oxidase. In the present work we report that 1) the catalytic center or the essential domains of dicarboxylyl-CoA synthetase are located at the cytosolic aspect of the endoplasmic reticulum membrane; 2) dicarboxylyl-CoA oxidase is optimally active on dodecanedioyl-CoA and is a peroxisomal enzyme; 3) cyanide-insensitive dodecanedioyl-CoA oxidation (NADH production) is catalyzed by rat liver homogenates. Cell fractionation studies disclose that, similar to dodecanedioyl-CoA oxidase (H2O2 production), the cyanide-insensitive dodecanedioyl-CoA oxidizing activity also belongs to peroxisomes; 4) a dodecanedioyl-CoA oxidoreductase reaction can be assayed by the dichlorphenolindophenol procedure in rat liver homogenates, and the activity is abundant in peroxisomal, mitochondrial, and soluble fractions; 5) by contrast with monocarboxylyl-CoA esters, the dicarboxylyl-CoAs are apparently not substrates for mitochondrial fatty acid oxidation; however, the use of dicarboxylylcarnitine esters as direct substrate for mitochondria suggests the existence of an active beta-oxidation of dicarboxylates in these organelles, which is further confirmed by experiments in which mitochondria are permeabilized with digitonin; 6) the in vivo oxidation of infused dodecanedioic acid results in a rapid appearance in urine of medium-chain dicarboxylic acids, with only 30-50% of the infused dose recovered in urine. << Less
Am J Physiol 256:G680-8(1989) [PubMed] [EuropePMC]
This publication is cited by 6 other entries.