2-Aminomuconic semialdehyde

2-Aminomuconic semialdehyde

Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name (2Z,4E)-2-Amino-6-oxohexa-2,4-dienoic acid
Identifiers
CAS Number	150994-59-5  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15745  Y
ChemSpider	4444230  Y
PubChem CID	30
InChI InChI=1S/C6H7NO3/c7-5(6(9)10)3-1-2-4-8/h1-4H,7H2,(H,9,10)/b2-1-,5-3+ Y Key: QCGTZPZKJPTAEP-REDYYMJGSA-N Y
SMILES C(=CC=O)C=C(C(=O)O)N
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]

2-Amino-3-carboxymuconic semialdehyde

 

 

CO₂

 

 

 

2-Aminomuconic semialdehyde

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

2-Aminomuconic semialdehyde

 

 

H₂O

 

 

 

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. 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 .