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2-Aminomuconic semialdehyde
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2-aminomuconic semialdehyde.png Skeletal formula 2-Aminomuconic-semialdehyde-3D-balls.png Ball-and-stick model (2Z,4E)-2-Amino-6-oxohexa-2,4-dienoic acid correct chemspider 4444230 correct chemspider 1S/C6H7NO3/c7-5(6(9)10)3-1-2-4-8/h1-4H,7H2,(H,9,10)/b2-1-,5-3+ correct chemspider QCGTZPZKJPTAEP-REDYYMJGSA-N correct CAS 150994-59-5 30 correct EBI 15745 C(=CC=O)C=C(C(=O)O)N
6 7 1 3 141.12 g/mol
2-Aminomuconic semialdehyde is a metabolite of tryptophan which is an unstable open-chain biochemical precursor of picolinic acid.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 10.1038/sj.jim.2900705 1476-5535 10510494 1091252 free 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 en 154 106646 10.1016/j.envint.2021.106646 34049269 0160-4120 free 2021EnInt.15406646Z Savitz J The kynurenine pathway: a finger in every pie. Molecular Psychiatry 25 January 2020 25 1 131–147 10.1038/s41380-019-0414-4 30980044 6790159
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.
50% Q2823201 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.Ichiyama Arata Nakamura Shigenobu Kawai Hitoshi Honjo Tasuku Nishizuka Yasutomi Hayaishi Osamu Senoh Siro Studies on the Metabolism of the Benzene Ring of Tryptophan in Mammalian Tissues Journal of Biological Chemistry 1965 240 2 740–749 10.1016/S0021-9258(17)45238-0 free
45% 2-Aminomuconic semialdehyde 1.2
H2O
Picolinic acid
See also
Muconic acid
Ommochrome
References
Category:Conjugated aldehydes
Category:Aldehydic acids
Category:Alpha-amino acids
Category:Enoic acids