3-Fumarylpyruvic acid
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| Preferred IUPAC name
(2E)-4,6-Dioxohept-2-enedioic acid | |
| Other names
(E)-4,6-Dioxohept-2-enedioic acid
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3D model (JSmol)
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CompTox Dashboard (EPA)
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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).
Infobox references
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3-Fumarylpyruvic acid, or 3-fumarylpyruvate, is a dicarboxylic acid formed from the isomerisation of 3-maleylpyruvate by maleylpyruvate isomerase.[1] It is converted into fumaric and pyruvic acids by 3-fumarylpyruvate hydrolase.[2]
Biosynthesis
3-Fumarylpyruvic acid is an intermediate in the metabolism of the amino acid tyrosine in some organisms. At an earlier stage, in the presence of the enzyme gentisate 1,2-dioxygenase and oxygen, gentisic acid undergoes a ring-opening reaction to give 3-maleylpyruvic acid:[3] This is converted to its geometric isomer by the enzyme maleylpyruvate isomerase.[1]
Metabolism
The metabolism of 3-fumarylpyruvic acid by the enzyme 3-fumarylpyruvate hydrolase involves its cleavage into fumaric and pyruvic acids.[2][4]
References
- ^ 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.
- ^ a b >Qu, Y. & Spain, J.C. (2011). "Molecular and biochemical characterization of the 5-nitroanthranilic acid degradation pathway in Bradyrhizobium sp. strain JS329". J. Bacteriol. 193 (12): 3057–3063. doi:10.1128/JB.01188-10. PMC 3133195. PMID 21498645.
- ^ 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.
- ^ Zhou NY, Fuenmayor SL, Williams PA (January 2001). "nag genes of Ralstonia (formerly Pseudomonas) sp. strain U2 encoding enzymes for gentisate catabolism". Journal of Bacteriology. 183 (2): 700–8. doi:10.1128/JB.183.2.700-708.2001. PMC 94927. PMID 11133965.