Maleylacetic acid

Chemical compound From Wikipedia, the free encyclopedia

Maleylacetic acid is a chemical compound produced in the biodegradation of catechin by Bradyrhizobium japonicum.[1]

Quick facts Names, Identifiers ...
Maleylacetic acid
Chemical structure of 2-maleylacetic acid
Chemical structure of maleylacetic acid
Names
IUPAC name
4-Oxohex-2-enedioic acid
Other names
2-Maleylacetic acid
Maleoylacetic acid
Identifiers
3D model (JSmol)
8404489
ChEBI
ChemSpider
KEGG
MeSH Maleoylacetic+acid
  • InChI=1S/C6H6O5/c7-4(3-6(10)11)1-2-5(8)9/h1-2H,3H2,(H,8,9)(H,10,11)
    Key: SOXXPQLIZIPMIZ-UHFFFAOYSA-N
  • OC(=O)CC(=O)C=CC(O)=O
Properties
C6H6O5
Molar mass 158.10 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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In Moraxella species, the compound is a product of the metabolism of hydroquinone, with the final step being from oxidation of 4-hydroxymuconic semialdehyde:[2]

2D representation of the chemical structure of Q27102979.
4-hydroxymuconic semialdehyde
+ NAD+
 
 
H2O
H+
Reversible left-right reaction arrow with minor forward substrate(s) from top left, minor forward product(s) to top right, minor reverse substrate(s) from bottom right and minor reverse product(s) to bottom left
H2O
H+
 
2D representation of the chemical structure of maleylacetic acid .
maleylacetic acid
+ NADH
 

The compound is reduced to 3-oxoadipic acid by the enzyme maleylacetate reductase in Trichosporon cutaneum:[3][4]

2D representation of the chemical structure of maleylacetic acid .
maleylacetic acid
+ NADH
 
 
H+
 
Reversible left-right reaction arrow with minor forward substrate(s) from top left and minor reverse product(s) to bottom left
H+
 
 
2D representation of the chemical structure of Q27117141.
3-oxoadipic acid
+ NAD+
 

References

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