2-Aminomuconic semialdehyde

2-Aminomuconic semialdehyde
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
(2Z,4E)-2-Amino-6-oxohexa-2,4-dienoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
InChI
  • InChI=1S/C6H7NO3/c7-5(6(9)10)3-1-2-4-8/h1-4H,7H2,(H,9,10)/b2-1-,5-3+ checkY
    Key: QCGTZPZKJPTAEP-REDYYMJGSA-N checkY
SMILES
  • C(=CC=O)C=C(C(=O)O)N
  • O=C\C=C\C=C(/N)C(=O)O
Properties
Chemical formula
 C6H7NO3
Molar mass 141.12 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2-Aminomuconic semialdehyde is a metabolite of tryptophan which is an unstable open-chain biochemical precursor of picolinic acid.[1][2][3]

Biochemistry

2-Aminomuconic semialdehyde is an intermediate in the kynurenine pathway of tryptophan metabolism, which leads to picolinic acid or quinolinic acid. The enzyme aminocarboxymuconate-semialdehyde decarboxylase produces it from 2-amino-3-carboxymuconic semialdehyde, a compound which would form quinolinic acid in the absence of that enzyme.[3]

2D representation of the chemical structure of Q2823201.
2-Amino-3-carboxymuconic semialdehyde
 
 
CO2
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of 2-Aminomuconic semialdehyde .
2-Aminomuconic semialdehyde

2-Aminomuconic semialdehyde itself is chemically unstable and spontaneously ring-closes to picolinic acid, with loss of water.[3][4]

2D representation of the chemical structure of 2-Aminomuconic semialdehyde.
2-Aminomuconic semialdehyde
 
 
H2O
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of Picolinic acid .
Picolinic acid

See also

  • Muconic acid
  • Ommochrome

References

  1. ^ He, Z.; Spain, J. (1999-08-01). "Preparation of 2-aminomuconate from 2-aminophenol by coupled enzymatic dioxygenation and dehydrogenation reactions". Journal of Industrial Microbiology & Biotechnology. 23 (2): 138–142. doi:10.1038/sj.jim.2900705. ISSN 1476-5535. PMID 10510494. S2CID 1091252.
  2. ^ Zeng, Ting; Liang, Yanshan; Chen, Jinyao; Cao, Guodong; Yang, Zhu; Zhao, Xingchen; Tian, Jinglin; Xin, Xiong; Lei, Bo; Cai, Zongwei (2021-09-01). "Urinary metabolic characterization with nephrotoxicity for residents under cadmium exposure". Environment International. 154 106646. Bibcode:2021EnInt.15406646Z. doi:10.1016/j.envint.2021.106646. ISSN 0160-4120. PMID 34049269.
  3. ^ a b c Savitz, J (25 January 2020). "The kynurenine pathway: a finger in every pie". Molecular Psychiatry. 25 (1): 131–147. doi:10.1038/s41380-019-0414-4. PMC 6790159. PMID 30980044.
  4. ^ Ichiyama, Arata; Nakamura, Shigenobu; Kawai, Hitoshi; Honjo, Tasuku; Nishizuka, Yasutomi; Hayaishi, Osamu; Senoh, Siro (1965). "Studies on the Metabolism of the Benzene Ring of Tryptophan in Mammalian Tissues". Journal of Biological Chemistry. 240 (2): 740–749. doi:10.1016/S0021-9258(17)45238-0.
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