4-Maleylacetoacetic acid
(Redirected from Maleylacetoacetate)
 | |
| Names | |
|---|---|
| Preferred IUPAC name
(2Z)-4,6-Dioxooct-2-enedioic acid | |
| Other names
4-Maleylacetoacetate | |
| Identifiers | |
3D model (JSmol) |
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| KEGG | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C8H8O6 | |
| Molar mass | 200.146 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
4-Maleylacetoacetate (4-maleylacetoacetatic acid) is an intermediate in the metabolism of tyrosine. It is converted to fumarylacetoacetic acid by the enzyme 4-maleylacetoacetate cis-trans-isomerase.
Biosynthesis
[edit]The amino acid tyrosine is metabolised in a series of reactions, one of which is catalysed by homogentisate 1,2-dioxygenase. This converts the intermediate homogentisic acid into 4-maleylacetoacetic acid.[1][2]
Metabolism
[edit]The enzyme maleylacetoacetate isomerase converts 4-maleylacetoacetic acid to its geometric isomer, fumarylacetoacetic acid.[3]
References
[edit]- ↑ Borowski, Tomasz; Georgiev, Valentin; Siegbahn, Per E. M. (2005). "Catalytic Reaction Mechanism of Homogentisate Dioxygenase: A Hybrid DFT Study". Journal of the American Chemical Society. 127 (49): 17303–17314. doi:10.1021/ja054433j. PMID 16332080.
- ↑ Timm, David E.; Titus, Greg P.; Mueller, Heather A.; Burgner, John; Rodríguez De Córdoba, Santiago; Peñalva, Miguel A. (2000). "Crystal structure of human homogentisate dioxygenase". Nature Structural Biology. 7 (7): 542–546. doi:10.1038/76756. PMID 10876237.
- ↑ Polekhina, Galina; Board, Philip G.; Blackburn, Anneke C.; Parker, Michael W. (2001). "Crystal Structure of Maleylacetoacetate Isomerase/Glutathione Transferase Zeta Reveals the Molecular Basis for Its Remarkable Catalytic Promiscuity". Biochemistry. 40 (6): 1567–1576. doi:10.1021/bi002249z. PMID 11327815.
 | This article about an alkene is a stub. You can help Wikipedia by adding missing information. |
.svg){kind=small} | This biochemistry article is a stub. You can help Wikipedia by adding missing information. |