2-Amino-3-carboxymuconic semialdehyde
Chemical compound
From Wikipedia, the free encyclopedia
2-Amino-3-carboxymuconic semialdehyde[1][2] is an intermediate in the metabolism of tryptophan in the kynurenine pathway. Quinolinic acid is a neurotoxin formed nonenzymatically from 2-amino-3-carboxymuconic semialdehyde in mammalian tissues. 2-Amino-3-carboxymuconic semialdehyde is enzymatically converted to picolinic acid via 2-aminomuconic semialdehyde.
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| Names | |
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| Preferred IUPAC name
(2Z)-2-Amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid | |
| Identifiers | |
3D model (JSmol) |
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CompTox Dashboard (EPA) |
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| Properties | |
| C7H7NO5 | |
| Molar mass | 185.13 g/mol |
| Density | 1.527 g/mL |
| Boiling point | 389 °C (732 °F; 662 K) |
| Hazards | |
| Flash point | 189 °C (372 °F; 462 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthesis
The enzyme 3-hydroxyanthranilate 3,4-dioxygenase uses oxygen to cleave the aromatic ring of 3-hydroxyanthranilic acid, giving 2-amino-3-carboxymuconic semialdehyde.[3]
Metabolism
The kynurenine pathway of tryptophan catabolism leads to nicotinamide adenine dinucleotide and supplies the nicotinic acid component of that cofactor.[3][4] In this pathway, quinolinic acid is produced spontaneously from the intermediate semialdehyde as its amine cyclises with the aldehyde, losing a molecule of water:[5]
Alternatively, 2-amino-3-carboxymuconic semialdehyde can be acted on by the enzyme aminocarboxymuconate-semialdehyde decarboxylase to give 2-aminomuconic semialdehyde, an unstable open-chain precursor of picolinic acid.[4][6][7][8]
