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Pathway Description
2-Oxopent-4-enoate Metabolism
Escherichia coli
Metabolic Pathway
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
Andreoni V, Bestetti G: Comparative analysis of different Pseudomonas strains that degrade cinnamic acid. Appl Environ Microbiol. 1986 Oct;52(4):930-4.
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
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