Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

MetaCyc Pathway: catechol degradation to 2-oxopent-4-enoate II

Enzyme View:

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: catechol degradation, meta-cleavage

Superclasses: Degradation/Utilization/Assimilation Aromatic Compounds Degradation Catechol Degradation

Some taxa known to possess this pathway include ? : Azotobacter vinelandii , Cupriavidus necator , Pseudomonas putida mt-2 , Pseudomonas sp. CF600

Expected Taxonomic Range: Actinobacteria , Proteobacteria

Summary:
Some bacteria catalyze the breakdown of catechol using one or more variants of the meta-cleavage pathway. For more discussion of this pathway, please see catechol degradation II (meta-cleavage pathway).

Superpathways: catechol degradation II (meta-cleavage pathway) , superpathway of aerobic toluene degradation , toluene degradation IV (aerobic) (via catechol) , meta cleavage pathway of aromatic compounds

Variants: aromatic compounds degradation via β-ketoadipate , catechol degradation I (meta-cleavage pathway) , catechol degradation III (ortho-cleavage pathway) , catechol degradation to 2-oxopent-4-enoate I , catechol degradation to β-ketoadipate

Credits:
Created 04-Dec-2006 by Caspi R , SRI International


References

SalaTrepat71: Sala-Trepat JM, Evans WC (1971). "The meta cleavage of catechol by Azotobacter species. 4-Oxalocrotonate pathway." Eur J Biochem 20(3);400-13. PMID: 4325686

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

Chen92b: Chen LH, Kenyon GL, Curtin F, Harayama S, Bembenek ME, Hajipour G, Whitman CP (1992). "4-Oxalocrotonate tautomerase, an enzyme composed of 62 amino acid residues per monomer." J Biol Chem 267(25);17716-21. PMID: 1339435

Harayama89: 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

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

Harayama93: Harayama S, Rekik M (1993). "Comparison of the nucleotide sequences of the meta-cleavage pathway genes of TOL plasmid pWW0 from Pseudomonas putida with other meta-cleavage genes suggests that both single and multiple nucleotide substitutions contribute to enzyme evolution." Mol Gen Genet 239(1-2);81-9. PMID: 8510667

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

Inoue95: Inoue J, Shaw JP, Rekik M, Harayama S (1995). "Overlapping substrate specificities of benzaldehyde dehydrogenase (the xylC gene product) and 2-hydroxymuconic semialdehyde dehydrogenase (the xylG gene product) encoded by TOL plasmid pWW0 of Pseudomonas putida." J Bacteriol 177(5);1196-201. PMID: 7868591

Junker94a: Junker F, Leisinger T, Cook AM (1994). "3-Sulphocatechol 2,3-dioxygenase and other dioxygenases (EC 1.13.11.2 and EC 1.14.12.-) in the degradative pathways of 2-aminobenzenesulphonic, benzenesulphonic and 4-toluenesulphonic acids in Alcaligenes sp. strain O-1." Microbiology 1994;140 ( Pt 7);1713-22. PMID: 8075807

Kasai09: Kasai D, Fujinami T, Abe T, Mase K, Katayama Y, Fukuda M, Masai E (2009). "Uncovering the Protocatechuate 2,3-Cleavage Pathway Genes." J Bacteriol 191(21):6758-6768. PMID: 19717587

Kohler93: Kohler HP, Schmid A, van der Maarel M (1993). "Metabolism of 2,2'-dihydroxybiphenyl by Pseudomonas sp. strain HBP1: production and consumption of 2,2',3-trihydroxybiphenyl." J Bacteriol 175(6);1621-8. PMID: 8449871

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

Muraki03: Muraki T, Taki M, Hasegawa Y, Iwaki H, Lau PC (2003). "Prokaryotic homologs of the eukaryotic 3-hydroxyanthranilate 3,4-dioxygenase and 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase in the 2-nitrobenzoate degradation pathway of Pseudomonas fluorescens strain KU-7." Appl Environ Microbiol 69(3);1564-72. PMID: 12620844

Nakai83: Nakai C, Hori K, Kagamiyama H, Nakazawa T, Nozaki M (1983). "Purification, subunit structure, and partial amino acid sequence of metapyrocatechase." J Biol Chem 258(5);2916-22. PMID: 6826545

Nakai83a: Nakai C, Kagamiyama H, Nozaki M, Nakazawa T, Inouye S, Ebina Y, Nakazawa A (1983). "Complete nucleotide sequence of the metapyrocatechase gene on the TOI plasmid of Pseudomonas putida mt-2." J Biol Chem 258(5);2923-8. PMID: 6826546

Orii06: Orii C, Takenaka S, Murakami S, Aoki K (2006). "Metabolism of 4-amino-3-hydroxybenzoic acid by Bordetella sp. strain 10d: A different modified meta-cleavage pathway for 2-aminophenols." Biosci Biotechnol Biochem 70(11);2653-61. PMID: 17090920

Roper94: Roper DI, Subramanya HS, Shingler V, Wigley DB (1994). "Preliminary crystallographic analysis of 4-oxalocrotonate tautomerase reveals the oligomeric structure of the enzyme." J Mol Biol 243(4);799-801. PMID: 7966298

Shaw90: Shaw JP, Harayama S (1990). "Purification and characterisation of TOL plasmid-encoded benzyl alcohol dehydrogenase and benzaldehyde dehydrogenase of Pseudomonas putida." Eur J Biochem 191(3);705-14. PMID: 2202600

Stanley00: Stanley TM, Johnson WH, Burks EA, Whitman CP, Hwang CC, Cook PF (2000). "Expression and stereochemical and isotope effect studies of active 4-oxalocrotonate decarboxylase." Biochemistry 39(4);718-26. PMID: 10651637

Subramanya96: Subramanya HS, Roper DI, Dauter Z, Dodson EJ, Davies GJ, Wilson KS, Wigley DB (1996). "Enzymatic ketonization of 2-hydroxymuconate: specificity and mechanism investigated by the crystal structures of two isomerases." Biochemistry 35(3);792-802. PMID: 8547259

Takenaka00: Takenaka S, Murakami S, Kim YJ, Aoki K (2000). "Complete nucleotide sequence and functional analysis of the genes for 2-aminophenol metabolism from Pseudomonas sp. AP-3." Arch Microbiol 174(4);265-72. PMID: 11081795

Taylor98a: Taylor AB, Czerwinski RM, Johnson WH, Whitman CP, Hackert ML (1998). "Crystal structure of 4-oxalocrotonate tautomerase inactivated by 2-oxo-3-pentynoate at 2.4 A resolution: analysis and implications for the mechanism of inactivation and catalysis." Biochemistry 37(42);14692-700. PMID: 9778344

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 SRI International Pathway Tools version 18.5 on Tue Nov 25, 2014, biocyc13.