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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Pathway: methylgallate degradation

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.

Superclasses: Degradation/Utilization/Assimilation Aromatic Compounds Degradation

Some taxa known to possess this pathway include ? : Comamonas testosteroni , Sphingomonas sp. SYK6

Expected Taxonomic Range: Bacteria

Summary:
Gallate, gallate esters, and compounds structurally related to them are widely distributed in nature. Plant lignin and tannins are major sources of these compounds, which are degraded by soil microorganisms as part of the terrestrial carbon cycle (in [Kasai04]). Fission of the benzene nucleus of gallate and its esters is catalyzed by bacterial dioxygenases. Several distinct pathways of aerobic aromatic catabolixm can be initiated by these dioxygenases, and their distribution among bacteria is complex [Gottschalk86]. Examples of these oxidative pathways are MetaCyc pathways gallate degradation II, gallate degradation I, protocatechuate degradation I (meta-cleavage pathway), protocatechuate degradation II (ortho-cleavage pathway), and superpathway of aromatic compound degradation via 3-oxoadipate. An anaerobic pathway for gallate degradation is shown in MetaCyc pathway gallate degradation III (anaerobic).

Cell suspensions of Comamonas testosteroni grown with 4-hydroxybenzoate contain induced protocatechuate 4,5-dioxygenase. This enzyme cleaves the benzene nucleus of 3-O-methylgallate by meta fission to produce 2-pyrone-4,6-dicarboxylate and methanol. Methanol was shown to be eliminated by the cells during pyrone formation, and a mechanism for this reaction was proposed. The 2-pyrone-4,6-dicarboxylate product of the dioxygenase is then degraded by 2-pyrone-4,6-dicarboxylate hydrolase. The product can spontaneously or enzymatically form the enol tautomer, (1Z,3Z)-4-hydroxybuta-1,3-diene-1,2,4-tricarboxylate. Hydration forms 2-hydroxy-4-oxobutane-1,2,4-tricarboxylate. Finally, an aldolase cleaves this compound to pyruvate and oxaloacetate, which enter central metabolism [Kersten82].

The hydrolase, hydratase, and aldolase also function in the protocatechuate meta cleavage pathway, and are enzymes central to aromatic compound degradation [Providenti01].

In Sphingomonas sp. SYK6 a dedicated 3-O-methylgallate 3,4-dioxygenase has been found (the product of the desZ gene). This enzyme catalyzes a similar ring fission reaction to the one catalyzed by protocatechuate 4,5-dioxygenase [Kasai04].

Credits:
Created 18-Jun-1998 by Ying HC , SRI International
Revised 24-Sep-2009 by Caspi R , SRI International


References

Gottschalk86: Gottschalk, G "Bacterial Metabolism, Second Edition." Springer-Verlag, New York. 1986.

Kasai04: Kasai D, Masai E, Miyauchi K, Katayama Y, Fukuda M (2004). "Characterization of the 3-O-methylgallate dioxygenase gene and evidence of multiple 3-O-methylgallate catabolic pathways in Sphingomonas paucimobilis SYK-6." J Bacteriol 186(15);4951-9. PMID: 15262932

Kersten82: Kersten PJ, Dagley S, Whittaker JW, Arciero DM, Lipscomb JD (1982). "2-pyrone-4,6-dicarboxylic acid, a catabolite of gallic acids in Pseudomonas species." J Bacteriol 1982;152(3);1154-62. PMID: 7142106

Providenti01: Providenti MA, Mampel J, MacSween S, Cook AM, Wyndham RC (2001). "Comamonas testosteroni BR6020 possesses a single genetic locus for extradiol cleavage of protocatechuate." Microbiology 147(Pt 8);2157-67. PMID: 11495993

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

Arciero83: Arciero DM, Lipscomb JD, Huynh BH, Kent TA, Munck E (1983). "EPR and Mossbauer studies of protocatechuate 4,5-dioxygenase. Characterization of a new Fe2+ environment." J Biol Chem 258(24);14981-91. PMID: 6317682

Dagley82: Dagley S (1982). "4-Hydroxy-4-methyl-2-ketoglutarate aldolase from Pseudomonas putida." Methods Enzymol 90 Pt E;272-6. PMID: 7154956

Hara00: Hara H, Masai E, Katayama Y, Fukuda M (2000). "The 4-oxalomesaconate hydratase gene, involved in the protocatechuate 4,5-cleavage pathway, is essential to vanillate and syringate degradation in Sphingomonas paucimobilis SYK-6." J Bacteriol 182(24);6950-7. PMID: 11092855

Hara03a: Hara H, Masai E, Miyauchi K, Katayama Y, Fukuda M (2003). "Characterization of the 4-carboxy-4-hydroxy-2-oxoadipate aldolase gene and operon structure of the protocatechuate 4,5-cleavage pathway genes in Sphingomonas paucimobilis SYK-6." J Bacteriol 185(1);41-50. PMID: 12486039

Kasai07: Kasai D, Masai E, Katayama Y, Fukuda M (2007). "Degradation of 3-O-methylgallate in Sphingomonas paucimobilis SYK-6 by pathways involving protocatechuate 4,5-dioxygenase." FEMS Microbiol Lett 274(2);323-8. PMID: 17645527

Kersten85: Kersten PJ, Chapman PJ, Dagley S (1985). "Enzymatic release of halogens or methanol from some substituted protocatechuic acids." J Bacteriol 162(2);693-7. PMID: 3988709

Kornberg61: Kornberg HL, Sadler JR "Metabolism of C2 compounds in micro-organisms." BiochemJ 1961;81:503-513.

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

Mampel05: Mampel J, Providenti MA, Cook AM (2005). "Protocatechuate 4,5-dioxygenase from Comamonas testosteroni T-2: biochemical and molecular properties of a new subgroup within class III of extradiol dioxygenases." Arch Microbiol 183(2);130-9. PMID: 15650824

Maruyama01: Maruyama K, Miwa M, Tsujii N, Nagai T, Tomita N, Harada T, Sobajima H, Sugisaki H (2001). "Cloning, sequencing, and expression of the gene encoding 4-hydroxy-4-methyl-2-oxoglutarate aldolase from Pseudomonas ochraceae NGJ1." Biosci Biotechnol Biochem 65(12);2701-9. PMID: 11826967

Maruyama83a: Maruyama K (1983). "Purification and properties of 2-pyrone-4,6-dicarboxylate hydrolase." J Biochem (Tokyo) 93(2);557-65. PMID: 6841353

Maruyama85: Maruyama K (1985). "Purification and properties of gamma-oxalomesaconate hydratase from Pseudomonas ochraceae grown with phthalate." Biochem Biophys Res Commun 128(1);271-7. PMID: 3985968

Maruyama90: Maruyama K (1990). "Purification and properties of 4-hydroxy-4-methyl-2-oxoglutarate aldolase from Pseudomonas ochraceae grown on phthalate." J Biochem (Tokyo) 1990;108(2);327-33. PMID: 2229032

Masai00: Masai E, Momose K, Hara H, Nishikawa S, Katayama Y, Fukuda M (2000). "Genetic and biochemical characterization of 4-carboxy-2-hydroxymuconate-6-semialdehyde dehydrogenase and its role in the protocatechuate 4,5-cleavage pathway in Sphingomonas paucimobilis SYK-6." J Bacteriol 182(23);6651-8. PMID: 11073908

Masai99: Masai E, Shinohara S, Hara H, Nishikawa S, Katayama Y, Fukuda M (1999). "Genetic and biochemical characterization of a 2-pyrone-4, 6-dicarboxylic acid hydrolase involved in the protocatechuate 4, 5-cleavage pathway of Sphingomonas paucimobilis SYK-6." J Bacteriol 181(1);55-62. PMID: 9864312

Noda90: Noda Y, Nishikawa S, Shiozuka K, Kadokura H, Nakajima H, Yoda K, Katayama Y, Morohoshi N, Haraguchi T, Yamasaki M (1990). "Molecular cloning of the protocatechuate 4,5-dioxygenase genes of Pseudomonas paucimobilis." J Bacteriol 172(5);2704-9. PMID: 2185230

Nogales10: Nogales, J., Canales, A., Jimenez-barbero, J., Serra, B., Pingarron, J. M., Garcia, J. L., Diaz, E. (2010). "Unravelling the gallic acid degradation pathway in bacteria: the gal cluster from Pseudomonas putida." Molecular Microbiology, 79:359-374. PMID: 21219457

Nogales11: Nogales J, Canales A, Jimenez-Barbero J, Serra B, Pingarron JM, Garcia JL, Diaz E (2011). "Unravelling the gallic acid degradation pathway in bacteria: the gal cluster from Pseudomonas putida." Mol Microbiol 79(2);359-74. PMID: 21219457

Park86: Park SH, Harris BG, Cook PF (1986). "pH dependence of kinetic parameters for oxalacetate decarboxylation and pyruvate reduction reactions catalyzed by malic enzyme." Biochemistry 25(13);3752-9. PMID: 3741834

Patil92: Patil RV, Dekker EE (1992). "Cloning, nucleotide sequence, overexpression, and inactivation of the Escherichia coli 2-keto-4-hydroxyglutarate aldolase gene." J Bacteriol 1992;174(1);102-7. PMID: 1339418

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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 Fri Nov 28, 2014, BIOCYC13B.