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Pathway Description
2-Oxopent-4-enoate Metabolism
Escherichia coli
Category:
Metabolite Pathway
Sub-Category:
Metabolic
Created: 2015-09-09
Last Updated: 2025-01-27
The pathway starts with trans-cinnamate interacting with a hydrogen ion, an oxygen molecule, and a NADH through a cinnamate dioxygenase resulting in a NAD and a cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol which then interact together through a 2,3-dihydroxy-2,3-dihydrophenylpropionate dehydrogenase resulting in the release of a hydrogen ion, an NADH molecule and a 2,3 dihydroxy-trans-cinnamate.
The second way by which the 2,3 dihydroxy-trans-cinnamate is acquired is through a 3-hydroxy-trans-cinnamate interacting with a hydrogen ion, a NADH and an oxygen molecule through a 3-(3-hydroxyphenyl)propionate 2-hydroxylase resulting in the release of a NAD molecule, a water molecule and a 2,3-dihydroxy-trans-cinnamate.
The compound 2,3 dihydroxy-trans-cinnamate then interacts with an oxygen molecule through a 2,3-dihydroxyphenylpropionate 1,2-dioxygenase resulting in a hydrogen ion and a 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate. The latter compound then interacts with a water molecule through a 2-hydroxy-6-oxononatrienedioate hydrolase resulting in a release of a hydrogen ion, a fumarate molecule and (2Z)-2-hydroxypenta-2,4-dienoate. The latter compound reacts spontaneously to isomerize into a 2-oxopent-4-enoate. This compound is then hydrated through a 2-oxopent-4-enoate hydratase resulting in a 4-hydroxy-2-oxopentanoate. This compound then interacts with a 4-hydroxy-2-ketovalerate aldolase resulting in the release of a pyruvate, and an acetaldehyde. The acetaldehyde then interacts with a coenzyme A and a NAD molecule through a acetaldehyde dehydrogenase resulting in a hydrogen ion, a NADH and an acetyl-coa which can be incorporated into the TCA cycle
References
2-Oxopent-4-enoate Metabolism References
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Pubmed: 3777934
Barnes MR, Duetz WA, Williams PA: A 3-(3-hydroxyphenyl)propionic acid catabolic pathway in Rhodococcus globerulus PWD1: cloning and characterization of the hpp operon. J Bacteriol. 1997 Oct;179(19):6145-53.
Pubmed: 9324265
Bugg TD: Overproduction, purification and properties of 2,3-dihydroxyphenylpropionate 1,2-dioxygenase from Escherichia coli. Biochim Biophys Acta. 1993 Oct 6;1202(2):258-64.
Pubmed: 8399388
Burlingame R, Chapman PJ: Catabolism of phenylpropionic acid and its 3-hydroxy derivative by Escherichia coli. J Bacteriol. 1983 Jul;155(1):113-21.
Pubmed: 6345502
Burlingame RP, Wyman L, Chapman PJ: Isolation and characterization of Escherichia coli mutants defective for phenylpropionate degradation. J Bacteriol. 1986 Oct;168(1):55-64.
Pubmed: 3531186
Dagley S, Chapman PJ, Gibson DT: The metabolism of beta-phenylpropionic acid by an Achromobacter. Biochem J. 1965 Dec;97(3):643-50.
Pubmed: 5881653
Diaz E, Ferrandez A, Prieto MA, Garcia JL: Biodegradation of aromatic compounds by Escherichia coli. Microbiol Mol Biol Rev. 2001 Dec;65(4):523-69, table of contents. doi: 10.1128/MMBR.65.4.523-569.2001.
Pubmed: 11729263
Diaz E, Ferrandez A, Garcia JL: Characterization of the hca cluster encoding the dioxygenolytic pathway for initial catabolism of 3-phenylpropionic acid in Escherichia coli K-12. J Bacteriol. 1998 Jun;180(11):2915-23.
Pubmed: 9603882
Ferrandez A, Garcia JL, Diaz E: Genetic characterization and expression in heterologous hosts of the 3-(3-hydroxyphenyl)propionate catabolic pathway of Escherichia coli K-12. J Bacteriol. 1997 Apr;179(8):2573-81.
Pubmed: 9098055
Strickland S, Massey V: The purification and properties of the flavoprotein melilotate hydroxylase. J Biol Chem. 1973 Apr 25;248(8):2944-52.
Pubmed: 4348920
Spence EL, Kawamukai M, Sanvoisin J, Braven H, Bugg TD: Catechol dioxygenases from Escherichia coli (MhpB) and Alcaligenes eutrophus (MpcI): sequence analysis and biochemical properties of a third family of extradiol dioxygenases. J Bacteriol. 1996 Sep;178(17):5249-56. doi: 10.1128/jb.178.17.5249-5256.1996.
Pubmed: 8752345
Ferrandez A, Garcia JL, Diaz E: Genetic characterization and expression in heterologous hosts of the 3-(3-hydroxyphenyl)propionate catabolic pathway of Escherichia coli K-12. J Bacteriol. 1997 Apr;179(8):2573-81. doi: 10.1128/jb.179.8.2573-2581.1997.
Pubmed: 9098055
Blattner FR, Plunkett G 3rd, Bloch CA, Perna NT, Burland V, Riley M, Collado-Vides J, Glasner JD, Rode CK, Mayhew GF, Gregor J, Davis NW, Kirkpatrick HA, Goeden MA, Rose DJ, Mau B, Shao Y: The complete genome sequence of Escherichia coli K-12. Science. 1997 Sep 5;277(5331):1453-62. doi: 10.1126/science.277.5331.1453.
Pubmed: 9278503
Yamamoto Y, Aiba H, Baba T, Hayashi K, Inada T, Isono K, Itoh T, Kimura S, Kitagawa M, Makino K, Miki T, Mitsuhashi N, Mizobuchi K, Mori H, Nakade S, Nakamura Y, Nashimoto H, Oshima T, Oyama S, Saito N, Sampei G, Satoh Y, Sivasundaram S, Tagami H, Horiuchi T, et al.: Construction of a contiguous 874-kb sequence of the Escherichia coli -K12 genome corresponding to 50.0-68.8 min on the linkage map and analysis of its sequence features. DNA Res. 1997 Apr 28;4(2):91-113. doi: 10.1093/dnares/4.2.91.
Pubmed: 9205837
Hayashi K, Morooka N, Yamamoto Y, Fujita K, Isono K, Choi S, Ohtsubo E, Baba T, Wanner BL, Mori H, Horiuchi T: Highly accurate genome sequences of Escherichia coli K-12 strains MG1655 and W3110. Mol Syst Biol. 2006;2:2006.0007. doi: 10.1038/msb4100049. Epub 2006 Feb 21.
Pubmed: 16738553
Pollard JR, Rialland D, Bugg TD: Substrate selectivity and biochemical properties of 4-hydroxy-2-keto-pentanoic acid aldolase from Escherichia coli. Appl Environ Microbiol. 1998 Oct;64(10):4093-4.
Pubmed: 9758851
This pathway was propagated using PathWhiz -
Pon, A. et al. Pathways with PathWhiz (2015) Nucleic Acids Res. 43(Web Server issue): W552–W559.
Propagated from SMP0001904
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