Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store

MetaCyc Pathway: 2-oxopentenoate degradation
Inferred from experiment

Enzyme View:

Pathway diagram: 2-oxopentenoate degradation

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: 2-oxopent-4-enoate degradation, 2-ketopentenoate degradation

Superclasses: Degradation/Utilization/AssimilationCarboxylates Degradation

Some taxa known to possess this pathway include : Acidovorax sp. JS42, Bordetella sp. 10d, Burkholderia cepacia, Comamonas sp. JS765, Escherichia coli K-12 substr. MG1655, Pseudomonas putida, Pseudomonas putida F1, Pseudomonas putida mt-2, Pseudomonas sp. CF600, Ralstonia pickettii

Expected Taxonomic Range: Proteobacteria

2-oxopent-4-enoate is a common intermediate in the aerobic degradation of many aromatic compounds, including catechol, toluene, naphthalene and dibenzofuran.

The degradation pathway depicted here has been described in several organisms, including Escherichia coli K-12. The genes encoding the enzymes of this pathway are often found on plasmids, such as naphthalene catabolic plasmids (pWW60-22 [Platt95] and pND6-1 [Li04a]), nitrobenzene catabolic plasmids (pNB1 and pNB2, [Park00]) and toluene catabolic plasmids (TOL) such as pWW102 [Aemprapa98].

In this pathway 2-oxopent-4-enoate is hydrolyzed to 4-hydroxy-2-oxopentanoate by the enzyme 2-oxopent-4-enoate hydratase. 4-hydroxy-2-oxopentanoate is broken into pyruvate and acetaldehyde, which is then converted to acetyl-CoA by acetaldehyde dehydrogenase [Harayama89a, Platt95].

Superpathways: naphthalene degradation to acetyl-CoA, mandelate degradation to acetyl-CoA, 3-phenylpropanoate and 3-(3-hydroxyphenyl)propanoate degradation, superpathway of aromatic compound degradation via 3-oxoadipate, superpathway of aromatic compound degradation via 2-oxopent-4-enoate, L-tryptophan degradation XII (Geobacillus), catechol degradation I (meta-cleavage pathway), catechol degradation II (meta-cleavage pathway), L-tryptophan degradation IX, p-cumate degradation, p-cymene degradation, toluene degradation II (aerobic) (via 4-methylcatechol), toluene degradation I (aerobic) (via o-cresol), toluene degradation V (aerobic) (via toluene-cis-diol), toluene degradation IV (aerobic) (via catechol), meta cleavage pathway of aromatic compounds, superpathway of aerobic toluene degradation

Unification Links: EcoCyc:PWY-5162

Created 04-May-2006 by Caspi R, SRI International


Aemprapa98: Aemprapa S, Williams PA (1998). "Implications of the xylQ gene of TOL plasmid pWW102 for the evolution of aromatic catabolic pathways." Microbiology 144 ( Pt 5);1387-96. PMID: 9611813

Harayama89a: Harayama S, Rekik M, Ngai KL, Ornston LN (1989). "Physically associated enzymes produce and metabolize 2-hydroxy-2,4-dienoate, a chemically unstable intermediate formed in catechol metabolism via meta cleavage in Pseudomonas putida." J Bacteriol 171(11);6251-8. PMID: 2681159

Li04a: Li W, Shi J, Wang X, Han Y, Tong W, Ma L, Liu B, Cai B (2004). "Complete nucleotide sequence and organization of the naphthalene catabolic plasmid pND6-1 from Pseudomonas sp. strain ND6." Gene 336(2);231-40. PMID: 15246534

Park00: Park HS, Kim HS (2000). "Identification and characterization of the nitrobenzene catabolic plasmids pNB1 and pNB2 in Pseudomonas putida HS12." J Bacteriol 182(3);573-80. PMID: 10633088

Platt95: Platt A, Shingler V, Taylor SC, Williams PA (1995). "The 4-hydroxy-2-oxovalerate aldolase and acetaldehyde dehydrogenase (acylating) encoded by the nahM and nahO genes of the naphthalene catabolic plasmid pWW60-22 provide further evidence of conservation of meta-cleavage pathway gene sequences." Microbiology 141 ( Pt 9);2223-33. PMID: 7496535

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

BRENDA14: BRENDA team (2014). Imported from BRENDA version existing on Aug 2014.

Burlingame83: Burlingame R, Chapman PJ (1983). "Stereospecificity in meta-fission catabolic pathways." J Bacteriol 155(1);424-6. PMID: 6345511

Burlingame83a: Burlingame R, Chapman PJ (1983). "Catabolism of phenylpropionic acid and its 3-hydroxy derivative by Escherichia coli." J Bacteriol 1983;155(1);113-21. PMID: 6345502

Clark80: Clark DP, Cronan JE (1980). "Acetaldehyde coenzyme A dehydrogenase of Escherichia coli." J Bacteriol 144(1);179-84. PMID: 6998946

Dellomonaco11: Dellomonaco C, Clomburg JM, Miller EN, Gonzalez R (2011). "Engineered reversal of the β-oxidation cycle for the synthesis of fuels and chemicals." Nature 476(7360);355-9. PMID: 21832992

DiazMejia09: Diaz-Mejia JJ, Babu M, Emili A (2009). "Computational and experimental approaches to chart the Escherichia coli cell-envelope-associated proteome and interactome." FEMS Microbiol Rev 33(1);66-97. PMID: 19054114

Eaton96: Eaton RW (1996). "p-Cumate catabolic pathway in Pseudomonas putida Fl: cloning and characterization of DNA carrying the cmt operon." J Bacteriol 1996;178(5);1351-62. PMID: 8631713

Ferrandez97: Ferrandez A, Garcia JL, Diaz E (1997). "Genetic characterization and expression in heterologous hosts of the 3-(3-hydroxyphenyl)propionate catabolic pathway of Escherichia coli K-12." J Bacteriol 1997;179(8);2573-81. PMID: 9098055

Fischer13: Fischer B, Boutserin S, Mazon H, Collin S, Branlant G, Gruez A, Talfournier F (2013). "Catalytic properties of a bacterial acylating acetaldehyde dehydrogenase: evidence for several active oligomeric states and coenzyme A activation upon binding." Chem Biol Interact 202(1-3);70-7. PMID: 23237860

GOA01: GOA, MGI (2001). "Gene Ontology annotation based on Enzyme Commission mapping." Genomics 74;121-128.

GOA01a: GOA, DDB, FB, MGI, ZFIN (2001). "Gene Ontology annotation through association of InterPro records with GO terms."

GOA06: GOA, SIB (2006). "Electronic Gene Ontology annotations created by transferring manual GO annotations between orthologous microbial proteins."

Guadalupe10: Guadalupe Medina V, Almering MJ, van Maris AJ, Pronk JT (2010). "Elimination of glycerol production in anaerobic cultures of a Saccharomyces cerevisiae strain engineered to use acetic acid as an electron acceptor." Appl Environ Microbiol 76(1);190-5. PMID: 19915031

Gupta00: Gupta S, Mat-Jan F, Latifi M, Clark DP (2000). "Acetaldehyde dehydrogenase activity of the AdhE protein of Escherichia coli is inhibited by intermediates in ubiquinone synthesis." FEMS Microbiol Lett 182(1);51-5. PMID: 10612730

Harayama91: Harayama S, Rekik M, Bairoch A, Neidle EL, Ornston LN (1991). "Potential DNA slippage structures acquired during evolutionary divergence of Acinetobacter calcoaceticus chromosomal benABC and Pseudomonas putida TOL pWW0 plasmid xylXYZ, genes encoding benzoate dioxygenases." J Bacteriol 1991;173(23);7540-8. PMID: 1938949

He99: He Z, Spain JC (1999). "Comparison of the downstream pathways for degradation of nitrobenzene by Pseudomonas pseudoalcaligenes JS45 (2-aminophenol pathway) and by Comamonas sp. JS765 (catechol pathway)." Arch Microbiol 171(5);309-16. PMID: 10382261

Kazahaya72: Kazahaya, T., Kawai, K., Yashima, S., Sasaki, Y. (1972). "Aerobic dissimilation of glucose by heterolactic bacteria III. Aldehyde dehydrogenase And alcohol dehydrogenase of Leuconostoc mesenteroides." J. Gen. Appl. Microbiol. 18:43-55.

Kessler91: Kessler D, Leibrecht I, Knappe J (1991). "Pyruvate-formate-lyase-deactivase and acetyl-CoA reductase activities of Escherichia coli reside on a polymeric protein particle encoded by adhE." FEBS Lett 281(1-2);59-63. PMID: 2015910

Kukor91: Kukor JJ, Olsen RH (1991). "Genetic organization and regulation of a meta cleavage pathway for catechols produced from catabolism of toluene, benzene, phenol, and cresols by Pseudomonas pickettii PKO1." J Bacteriol 1991;173(15);4587-94. PMID: 1856161

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Showing only 20 references. To show more, press the button "Show all references".

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Wed May 4, 2016, biocyc13.