3-Maleylpyruvic acid

3-Maleylpyruvic acid
Names
Preferred IUPAC name
(2Z)-4,6-Dioxohept-2-enedioic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference
 1725756
ChEBI
ChemSpider
KEGG
PubChem CID
InChI
  • InChI=1S/C7H6O6/c8-4(1-2-6(10)11)3-5(9)7(12)13/h1-2H,3H2,(H,10,11)(H,12,13)/b2-1-
    Key: AZCFLHZUFANAOR-UPHRSURJSA-N
SMILES
  • C(C(=O)/C=C\C(=O)O)C(=O)C(=O)O
Properties
Chemical formula
 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).
Infobox references

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]

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]

2D representation of the chemical structure of gentisic acid .
gentisic acid
 
O2
 
Rightward reaction arrow with minor substrate(s) from top left
 
 
 
2D representation of the chemical structure of 3-Maleylpyruvic acid.
3-maleylpyruvic acid

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]

2D representation of the chemical structure of 3-Maleylpyruvic acid.
cis isomer
 
 
 
Reversible left-right reaction arrow
 
 
 
2D representation of the chemical structure of 3-Fumarylpyruvic acid.
trans isomer

References

  1. ^ a b Sugiyama, Shin-ich; Yano, Keiji; Komagata, Kazuo; Arima, Kei (1960). "Metabolism of Aromatic Compounds by Microbes". Bulletin of the Agricultural Chemical Society of Japan. 24 (3): 243–248. doi:10.1271/bbb1924.24.243.
  2. ^ a b Lack L (November 1961). "Enzymic cis-trans isomerization of maleylpyruvic acid". The Journal of Biological Chemistry. 236 (11): 2835–40. doi:10.1016/S0021-9258(19)76386-8. PMID 14461395.
  3. ^ Kutraite, I; Augustiniene, E; Malys,N (2024). "Maleylpyruvic Acid-Inducible Gene Expression System and Its Application for the Development of Gentisic Acid Biosensors". Analytical Chemistry. 96 (47): 18727–35. doi:10.1021/acs.analchem.4c03906. PMC 11603403. PMID 39548649.
  4. ^ Enzyme 5.2.1.4 at KEGG Pathway Database.
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