3-Maleylpyruvic acid
Chemical compound
From Wikipedia, the free encyclopedia
3-Maleylpyruvic acid, or 3-maleylpyruvate, is a dicarboxylic acid formed by the oxidative ring opening of gentisic acid by gentisate 1,2-dioxygenase during the metabolism of tyrosine.[1] It is converted into 3-fumarylpyruvate by maleylpyruvate isomerase.[2]
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| Names | |
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| Preferred IUPAC name
(2Z)-4,6-Dioxohept-2-enedioic acid | |
| Identifiers | |
3D model (JSmol) |
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| 1725756 | |
| ChEBI | |
| ChemSpider | |
| KEGG | |
PubChem CID |
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| Properties | |
| C7H6O6 | |
| Molar mass | 186.119 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthesis
In some organisms, the amino acid tyrosine is metabolised to gentisic acid. In the presence of the enzyme gentisate 1,2-dioxygenase and oxygen, this compound undergoes a ring-opening reaction to give 3-maleylpyruvic acid:[1]
This reaction has been used to detect gentisic acid with a whole-cell biosensor developed from a 3-maleylpyruvic acid-inducible gene expression system and the gentisate 1,2-dioxygenase gene from chemolithoautotrophic bacterium Cupriavidus necator.[3]
Metabolism
The enzyme maleylpyruvate isomerase converts 3-maleylpyruvic acid to its geometric isomer, 3-fumarylpyruvic acid.[4][2]
