Reaction participants Show >> << Hide
- Name help_outline (2R,3S)-2,3-dimethylmalate Identifier CHEBI:57422 Charge -2 Formula C6H8O5 InChIKeyhelp_outline WTIIULQJLZEHGZ-AWFVSMACSA-L SMILEShelp_outline C[C@H](C([O-])=O)[C@@](C)(O)C([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 dimethylmaleate Identifier CHEBI:17081 (Beilstein: 3664409) help_outline Charge -2 Formula C6H6O4 InChIKeyhelp_outline CGBYBGVMDAPUIH-ARJAWSKDSA-L SMILEShelp_outline C\C(C([O-])=O)=C(/C)C([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 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:20253 | RHEA:20254 | RHEA:20255 | RHEA:20256 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Nicotinic acid metabolism. Dimethylmaleate hydratase.
Kollmann-Koch A., Eggerer H.
The partial enrichment of a new enzyme, dimethylmaleate hydratase from Clostridium barkeri and some of its characteristics are described. The unstable and oxygen-sensitive hydratase depends on ferrous ions and is induced during growth of C. barkeri on nicotinic acid. The enzyme uses both dimethylm ... >> More
The partial enrichment of a new enzyme, dimethylmaleate hydratase from Clostridium barkeri and some of its characteristics are described. The unstable and oxygen-sensitive hydratase depends on ferrous ions and is induced during growth of C. barkeri on nicotinic acid. The enzyme uses both dimethylmaleate and the hydration product, 2,3-dimethylmalate, as substrates to establish an equilibrium that is 70% in favour of the latter acid; dimethylfumarate is not attacked. A 2,3-dimethyl[3-3H]malate specimen was prepared from dimethylmaleate with the hydratase in tritiated water. Based on proton attack at the re-face of the double bond, experimental results indicate the (2R,3S)-configuration for this malate. The hydration reaction takes an anti-course. The tritium label was lost in the sequence (2R,3S)-2,3-dimethyl[3-3H]malate----(R)-[2-3H1]-propionate----(2R) - [2-3H1]propionyl-CoA----(2S)-methylmalonyl-CoA. This result confirms the stereochemical course of the 2,3-dimethylmalate lyase reaction, inversion of configuration, by an independent approach. The hydratase reaction completes the degradation scheme of nicotinic acid by C. barkeri. The pathway is briefly reviewed. << Less
Hoppe-Seyler's Z. Physiol. Chem. 365:847-857(1984) [PubMed] [EuropePMC]