4-Maleylacetoacetic acid

4-Maleylacetoacetic acid
Names
	Preferred IUPAC name (2Z)-4,6-Dioxooct-2-enedioic acid
	Other names 4-Maleylacetoacetate
Identifiers
CAS Number	5698-52-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:47904 ;
ChEMBL	ChEMBL1743220 ;
ChemSpider	4444078 ;
KEGG	C01036 ;
PubChem CID	5280393;
UNII	5ET93TW8TE ;
CompTox Dashboard (EPA)	DTXSID201299688 ;
	InChI InChI=1S/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1- Key: GACSIVHAIFQKTC-UPHRSURJSA-N ;
	SMILES O=C(/C=C\C(=O)O)CC(=O)CC(=O)O;
Properties
Chemical formula	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). Infobox references

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

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]

Homogentisic acid

O₂

4-Maleylacetoacetic acid

Metabolism

The enzyme maleylacetoacetate isomerase converts 4-maleylacetoacetic acid to its geometric isomer, fumarylacetoacetic acid.^[3]

4-Maleylacetoacetic acid

Fumarylacetoacetic acid

References

^ 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.

[1] 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.

[2] 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.

[3] 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.

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