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discounted EARLY registration ends Dec 31, 2014
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
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for maintenance.
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discounted EARLY registration ends Dec 31, 2014
BioCyc websites MAYBE down
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Escherichia coli K-12 substr. MG1655 Pathway: 3-phenylpropanoate and 3-(3-hydroxyphenyl)propanoate degradation to 2-oxopent-4-enoate

If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Locations of Mapped Genes:

Genetic Regulation Schematic: ?

Synonyms: 3-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoate

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

Summary:
Different strains of E. coli have the ability to utilize certain aromatic acids as the sole source of carbon. Shown here, E. coli K-12 can grow on both 3-phenylpropanoate and 3-(3-hydroxyphenyl)propionate [Burlingame83]. For the complete degradation pathway, please see the superpathway 3-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation.

Note that MhpB and MhpC are the only enzymes in this pathway that have been biochemically characterized.

Superpathways: 3-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation

Credits:
Created 16-May-1996 by Riley M , Marine Biological Laboratory
Last-Curated ? 27-Oct-2011 by Keseler I , SRI International


References

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

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

Boxhammer08: Boxhammer S, Glaser S, Kuhl A, Wagner AK, Schmidt CL (2008). "Characterization of the recombinant Rieske [2Fe-2S] proteins HcaC and YeaW from E. coli." Biometals 21(4):459-67. PMID: 18286376

Bugg93: Bugg TD (1993). "Overproduction, purification and properties of 2,3-dihydroxyphenylpropionate 1,2-dioxygenase from Escherichia coli." Biochim Biophys Acta 1993;1202(2);258-64. PMID: 8399388

Burlingame86: Burlingame RP, Wyman L, Chapman PJ (1986). "Isolation and characterization of Escherichia coli mutants defective for phenylpropionate degradation." J Bacteriol 1986;168(1);55-64. PMID: 3531186

Diaz98: Diaz E, Ferrandez A, Garcia JL (1998). "Characterization of the hca cluster encoding the dioxygenolytic pathway for initial catabolism of 3-phenylpropionic acid in Escherichia coli K-12." J Bacteriol 1998;180(11);2915-23. PMID: 9603882

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

Dunn05: Dunn G, Montgomery MG, Mohammed F, Coker A, Cooper JB, Robertson T, Garcia JL, Bugg TD, Wood SP (2005). "The structure of the C-C bond hydrolase MhpC provides insights into its catalytic mechanism." J Mol Biol 346(1);253-65. PMID: 15663942

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

Fleming00: Fleming SM, Robertson TA, Langley GJ, Bugg TD (2000). "Catalytic mechanism of a C-C hydrolase enzyme: evidence for a gem-diol intermediate, not an acyl enzyme." Biochemistry 39(6);1522-31. PMID: 10684634

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."

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

Henderson97: Henderson IM, Bugg TD (1997). "Pre-steady-state kinetic analysis of 2-hydroxy-6-keto-nona-2,4-diene-1,9-dioic acid 5,6-hydrolase: kinetic evidence for enol/keto tautomerization." Biochemistry 36(40);12252-8. PMID: 9315863

Lam94: Lam WWY, Bugg TDH (1994). "Chemistry of extradiol aromatic ring cleavage: Isolation of a stable dienol ring fission intermediate and stereochemistry of its enzymatic hydrolytic cleavage." J Chem Soc, Chem Commun (1994): 1163-1164.

Lam97: Lam WW, Bugg TD (1997). "Purification, characterization, and stereochemical analysis of a C-C hydrolase: 2-hydroxy-6-keto-nona-2,4-diene-1,9-dioic acid 5,6-hydrolase." Biochemistry 36(40);12242-51. PMID: 9315862

Li05: Li C, Montgomery MG, Mohammed F, Li JJ, Wood SP, Bugg TD (2005). "Catalytic mechanism of C-C hydrolase MhpC from Escherichia coli: kinetic analysis of His263 and Ser110 site-directed mutants." J Mol Biol 346(1);241-51. PMID: 15663941

Li06: Li JJ, Li C, Blindauer CA, Bugg TD (2006). "Evidence for a gem-diol reaction intermediate in bacterial C-C hydrolase enzymes BphD and MhpC from 13C NMR spectroscopy." Biochemistry 45(41);12461-9. PMID: 17029401

Li06a: Li C, Li JJ, Montgomery MG, Wood SP, Bugg TD (2006). "Catalytic role for arginine 188 in the C-C hydrolase catalytic mechanism for Escherichia coli MhpC and Burkholderia xenovorans LB400 BphD." Biochemistry 45(41);12470-9. PMID: 17029402

Li08: Li C, Hassler M, Bugg TD (2008). "Catalytic promiscuity in the alpha/beta-hydrolase superfamily: hydroxamic acid formation, C--C bond formation, ester and thioester hydrolysis in the C--C hydrolase family." Chembiochem 9(1);71-6. PMID: 18058773

Mendel04: Mendel S, Arndt A, Bugg TD (2004). "Acid-base catalysis in the extradiol catechol dioxygenase reaction mechanism: site-directed mutagenesis of His-115 and His-179 in Escherichia coli 2,3-dihydroxyphenylpropionate 1,2-dioxygenase (MhpB)." Biochemistry 43(42);13390-6. PMID: 15491145

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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