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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
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MetaCyc Pathway: 4-hydroxyphenylacetate 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.

Synonyms: 4-HPA degradation, homoprotocatechuate degradation

Superclasses: Degradation/Utilization/Assimilation Aromatic Compounds Degradation

Some taxa known to possess this pathway include ? : Acinetobacter , Escherichia coli B , Escherichia coli C , Escherichia coli W , Klebsiella pneumoniae , Pseudomonas aeruginosa PAO1 , Pseudomonas putida , Pseudomonas putida U

Expected Taxonomic Range: Proteobacteria

Summary:
4-hydroxyphenylacetate is a common product of aromatic amino acids fermentation (see tyrosine degradation II). It is also produced during the degradation of some plant materials in animal intestinal tracts [Diaz01]. Several bacteria are capable of degrading 4-hydroxyphenylacetate by first converting it into 3,4-dihydroxyphenylacetate (homoprotocatechuate), which is then degraded into TCA cycle internediates via an inducible meta-cleavage pathway that provides both a carbon source and energy to the bacteria [Sparnins74, Martin91].

This pathway is found in several Escherichia coli strains, including Escherichia coli B, Escherichia coli C and Escherichia coli W, but not Escherichia coli K-12 [Burlingame83]. Some, but not all, strains can also catabolize 3-hydroxyphenylacetate via the same pathway [Cooper80].

The genes encoding the enzymes of this pathway are located in Escherichia coli in two operons. The first operon includes hpaABC, and is induced by the presence of 4-hydroxyphenylacetate. The rest of the genes are located in a second operon, and are induced by 3,4-dihydroxyphenylacetate [Prieto96]. This second operon has been named either hpa or hpc operon in Escherichia coli W and Escherichia coli C, respectively.

In Escherichia coli the expression of these operons is controlled by the Pg promoter, which is regulated by both CRP (cAMP receptor protein)and IHF (integration host factor) [Barrett75].

Citations: [Overbeek98]

Credits:
Created 22-Jun-1998 by Ying HC , SRI International
Revised 30-Nov-2006 by Caspi R , SRI International


References

Barrett75: Barrett J, Dawidson I, Dhurandhar HN, Miller E, Litwin MS (1975). "Pulmonary microembolism associated with massive transfusion: II. The basic pathophysiology of its pulmonary effects." Ann Surg 182(1);56-61. PMID: 1147710

Burlingame83: 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

Cooper80: Cooper RA, Skinner MA (1980). "Catabolism of 3- and 4-hydroxyphenylacetate by the 3,4-dihydroxyphenylacetate pathway in Escherichia coli." J Bacteriol 143(1);302-6. PMID: 6995433

Diaz01: Diaz E, Ferrandez A, Prieto MA, Garcia JL (2001). "Biodegradation of aromatic compounds by Escherichia coli." Microbiol Mol Biol Rev 65(4);523-69, table of contents. PMID: 11729263

Martin91: Martin M, Gibello A, Fernandez J, Ferrer E, Garrido-Pertierra A (1991). "Catabolism of 3- and 4-hydroxyphenylacetic acid by Klebsiella pneumoniae." J Gen Microbiol 137(3);621-8. PMID: 1851804

Overbeek98: Overbeek, R, Larsen, N, Selkov, EE, Maltsev, M "The WIT Database." 1998 WWW URL http://www.cme.msu.edu/WIT/.

Prieto96: Prieto MA, Diaz E, Garcia JL (1996). "Molecular characterization of the 4-hydroxyphenylacetate catabolic pathway of Escherichia coli W: engineering a mobile aromatic degradative cluster." J Bacteriol 1996;178(1);111-20. PMID: 8550403

Roper93: Roper DI, Fawcett T, Cooper RA (1993). "The Escherichia coli C homoprotocatechuate degradative operon: hpc gene order, direction of transcription and control of expression." Mol Gen Genet 237(1-2);241-50. PMID: 8384293

Sparnins74: Sparnins VL, Chapman PJ, Dagley S (1974). "Bacterial degradation of 4-hydroxyphenylacetic acid and homoprotocatechuic acid." J Bacteriol 120(1);159-67. PMID: 4420192

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

Alonso82: Alonso JM, Garrido-Pertierra A (1982). "Carboxymethylhydroxymuconic semialdehyde dehydrogenase in the 4-hydroxyphenylacetate catabolic pathway of Escherichia coli." Biochim Biophys Acta 719(1);165-7. PMID: 6756482

Bartsch90: Bartsch K, von Johnn-Marteville A, Schulz A (1990). "Molecular analysis of two genes of the Escherichia coli gab cluster: nucleotide sequence of the glutamate:succinic semialdehyde transaminase gene (gabT) and characterization of the succinic semialdehyde dehydrogenase gene (gabD)." J Bacteriol 1990;172(12);7035-42. PMID: 2254272

BRENDA14: BRENDA team (2014). "Imported from BRENDA version existing on Aug 2014." http://www.brenda-enzymes.org.

Chiribau06: Chiribau CB, Mihasan M, Ganas P, Igloi GL, Artenie V, Brandsch R (2006). "Final steps in the catabolism of nicotine." FEBS J 273(7);1528-36. PMID: 16689938

Cozzani80: Cozzani I, Fazio AM, Felici E, Barletta G (1980). "Separation and characterization of NAD- and NADP-specific succinate-semialdehyde dehydrogenase from Escherichia coli K-12 3300." Biochim Biophys Acta 613(2);309-17. PMID: 7004491

deCarvalho11: de Carvalho LP, Ling Y, Shen C, Warren JD, Rhee KY (2011). "On the chemical mechanism of succinic semialdehyde dehydrogenase (GabD1) from Mycobacterium tuberculosis." Arch Biochem Biophys 509(1);90-9. PMID: 21303655

Donnelly81: Donnelly MI, Cooper RA (1981). "Two succinic semialdehyde dehydrogenases are induced when Escherichia coli K-12 Is grown on gamma-aminobutyrate." J Bacteriol 1981;145(3);1425-7. PMID: 7009588

Dover72: Dover S, Halpern YS (1972). "Control of the pathway of -aminobutyrate breakdown in Escherichia coli K-12." J Bacteriol 110(1);165-70. PMID: 4552985

Ferrer88: Ferrer, E., Cooper, R. A. (1988). "Studies with a cloned Escherichia coli C 2-oxo-hept-3-ene-1,7-dioate hydratase gene." FEMS Microbiol. Let. 52: 155-160.

Galan00: Galan B, Diaz E, Prieto MA, Garcia JL (2000). "Functional analysis of the small component of the 4-hydroxyphenylacetate 3-monooxygenase of Escherichia coli W: a prototype of a new Flavin:NAD(P)H reductase subfamily." J Bacteriol 182(3);627-36. PMID: 10633095

GarridoPeritier81: Garrido-Peritierra A, Cooper RA (1981). "Identification and purification of distinct isomerase and decarboxylase enzymes involved in the 4-hydroxyphenylacetate catabolic pathway of Escherichia coli." Eur J Biochem 1981;117(3);581-4. PMID: 7026235

Gibello94: Gibello A, Ferrer E, Martin M, Garrido-Pertierra A (1994). "3,4-Dihydroxyphenylacetate 2,3-dioxygenase from Klebsiella pneumoniae, a Mg(2+)-containing dioxygenase involved in aromatic catabolism." Biochem J 301 ( Pt 1);145-50. PMID: 8037662

Jaeger08: Jaeger M, Rothacker B, Ilg T (2008). "Saturation transfer difference NMR studies on substrates and inhibitors of succinic semialdehyde dehydrogenases." Biochem Biophys Res Commun 372(3);400-6. PMID: 18474219

Langendorf10: Langendorf CG, Key TL, Fenalti G, Kan WT, Buckle AM, Caradoc-Davies T, Tuck KL, Law RH, Whisstock JC (2010). "The X-ray crystal structure of Escherichia coli succinic semialdehyde dehydrogenase; structural insights into NADP+/enzyme interactions." PLoS One 5(2);e9280. PMID: 20174634

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

Liebgott09: Liebgott PP, Amouric A, Comte A, Tholozan JL, Lorquin J (2009). "Hydroxytyrosol from tyrosol using hydroxyphenylacetic acid-induced bacterial cultures and evidence of the role of 4-HPA 3-hydroxylase." Res Microbiol 160(10);757-66. PMID: 19837158

Lin12b: Lin Y, Yan Y (2012). "Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex." Microb Cell Fact 11;42. PMID: 22475509

Lin13a: Lin Y, Sun X, Yuan Q, Yan Y (2013). "Combinatorial biosynthesis of plant-specific coumarins in bacteria." Metab Eng 18;69-77. PMID: 23644174

Lobo02: Lobo C, Sanchez M, Garbi C, Ferrer E, Martinez-Inigo MJ, Allende JL, Martin C, Casasus L, Alonso R, Gibello A, Martin M (2002). "Immobilized native bacteria as a tool for bioremediation of soils and waters: implementation and modeling." ScientificWorldJournal 2;1361-8. PMID: 12805921

Louie03: Louie TM, Xie XS, Xun L (2003). "Coordinated production and utilization of FADH2 by NAD(P)H-flavin oxidoreductase and 4-hydroxyphenylacetate 3-monooxygenase." Biochemistry 42(24);7509-17. PMID: 12809507

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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 Sun Nov 23, 2014, biocyc14.