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MetaCyc Pathway: 3-phenylpropanoate degradation
Inferred from experiment

Pathway diagram: 3-phenylpropanoate 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: 3-phenylpropionate degradation, 3-phenylpropionic acid degradation

Superclasses: Degradation/Utilization/AssimilationAromatic Compounds DegradationPhenolic Compounds Degradation

Some taxa known to possess this pathway include : Haloferax sp. D1227

Expected Taxonomic Range: Archaea, Bacteria

3-Phenylpropionate is a natural environmental compound produced by degradation of organic matter, including plant lignin. Bacterial catabolism of this aromatic compound has been studied in several genera. An Escherichia coli K12 pathway for degradation of 3-phenylpropionate is shown in MetaCyc pathway 3-phenylpropanoate and 3-(3-hydroxyphenyl)propanoate degradation to 2-oxopent-4-enoate. The organism in the pathway shown here, the aerobic archaeon Haloferax sp. D1227, is an extreme halophile isolated from soil contaminated with saline oil brine [Fu99].

Haloferax sp. D1227 is able to utilize aromatic compounds as sole carbon and energy sources. This pathway represents a proposed pathway for degrading 3-phenylpropionic acid. The unstable intermediates, 3-hydroxy-3-phenylpropionyl-CoA and 3-keto-3-phenylpropionyl-CoA, were not detected in a biochemical study, but the conversion of cinnamyl-CoA to benzoyl-CoA did occur. [Fu99]

The first segment of the pathway, converting 3-phenylpropionate to benzoyl-CoA, is similar to fatty acid β-oxidation. Three of the reactions are labeled here as hypothetical due to lack of detection of the unstable intermediates. However, the conversion of cinnamyl-CoA to benzoyl-CoA was shown to be NAD-dependent. [Fu99]

The formation of the dihydroxylated intermediate, 2,5-dihydroxybenzoate (gentisate), followed by ring cleavage by gentisate dioxygenase, is characteristic of bacterial aerobic degradation of aromatic compounds. No hydroxylase activities for the conversion of benzoyl-CoA to 3-hydroxybenzoyl-CoA, and 3-hydroxybenzoyl-CoA to 2,5-dihydroxybenzoate were detected, although the metabolites 3-hydroxybenzoate and 2,5-dihydroxybenzoate (gentisate) were identified. The two segments of the pathway are regulated separately, by inducible enzymes [Fu99]. In Pseudomonas, the product of the cis-trans isomerase, 3-fumarylpyruvate, has been shown to be further metabolized by hydrolysis to fumarate and pyruvate [Lack61].

Subpathways: gentisate degradation I


Fu99: Fu W, Oriel P (1999). "Degradation of 3-phenylpropionic acid by Haloferax sp. D1227." Extremophiles 1999;3(1);45-53. PMID: 10086844

Lack61: Lack, L. (1961). "Enzymic cis-trans isomerization of maleylpyruvic acid." J Biol Chem 236;2835-40. PMID: 14461395

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

Bayly80: Bayly RC, Chapman PJ, Dagley S, Di Berardino D (1980). "Purification and some properties of maleylpyruvate hydrolase and fumarylpyruvate hydrolase from Pseudomonas alcaligenes." J Bacteriol 143(1);70-7. PMID: 7400101

Crawford77: Crawford RL, Frick TD (1977). "Rapid spectrophotometric differentiation between glutathione-dependent and glutathione-independent gentisate and homogentisate pathways." Appl Environ Microbiol 34(2);170-4. PMID: 907340

Dean08: Dean JV, Delaney SP (2008). "Metabolism of salicylic acid in wild-type, ugt74f1 and ugt74f2 glucosyltransferase mutants of Arabidopsis thaliana." Physiol Plant 132(4);417-25. PMID: 18248508

Feng06: Feng J, Che Y, Milse J, Yin YJ, Liu L, Ruckert C, Shen XH, Qi SW, Kalinowski J, Liu SJ (2006). "The gene ncgl2918 encodes a novel maleylpyruvate isomerase that needs mycothiol as cofactor and links mycothiol biosynthesis and gentisate assimilation in Corynebacterium glutamicum." J Biol Chem 281(16);10778-85. PMID: 16481315

Feng99: Feng Y, Khoo HE, Poh CL (1999). "Purification and characterization of gentisate 1,2-dioxygenases from Pseudomonas alcaligenes NCIB 9867 and Pseudomonas putida NCIB 9869." Appl Environ Microbiol 65(3);946-50. PMID: 10049846

Fu98: Fu W, Oriel P (1998). "Gentisate 1,2-dioxygenase from Haloferax sp. D1227." Extremophiles 2(4);439-46. PMID: 9827334

Fuenmayor98: Fuenmayor SL, Wild M, Boyes AL, Williams PA (1998). "A gene cluster encoding steps in conversion of naphthalene to gentisate in Pseudomonas sp. strain U2." J Bacteriol 180(9);2522-30. PMID: 9573207

Goetz92: Goetz FE, Harmuth LJ (1992). "Gentisate pathway in Salmonella typhimurium: metabolism of m-hydroxybenzoate and gentisate." FEMS Microbiol Lett 76(1-2);45-9. PMID: 1427003

Grund92: Grund E, Denecke B, Eichenlaub R (1992). "Naphthalene degradation via salicylate and gentisate by Rhodococcus sp. strain B4." Appl Environ Microbiol 58(6);1874-7. PMID: 1622263

Hopper68: Hopper DJ, Chapman PJ, Dagley S (1968). "Enzymic formation of D-malate." Biochem J 110(4);798-800. PMID: 5704827

Ishiyama04: Ishiyama D, Vujaklija D, Davies J (2004). "Novel pathway of salicylate degradation by Streptomyces sp. strain WA46." Appl Environ Microbiol 70(3);1297-306. PMID: 15006746

Jones90a: Jones DC, Cooper RA (1990). "Catabolism of 3-hydroxybenzoate by the gentisate pathway in Klebsiella pneumoniae M5a1." Arch Microbiol 154(5);489-95. PMID: 2256782

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

Monticello85: Monticello DJ, Bakker D, Schell M, Finnerty WR (1985). "Plasmid-borne Tn5 insertion mutation resulting in accumulation of gentisate from salicylate." Appl Environ Microbiol 49(4);761-4. PMID: 2988437

Moore02: Moore BS, Hertweck C, Hopke JN, Izumikawa M, Kalaitzis JA, Nilsen G, O'Hare T, Piel J, Shipley PR, Xiang L, Austin MB, Noel JP (2002). "Plant-like biosynthetic pathways in bacteria: from benzoic acid to chalcone." J Nat Prod 65(12);1956-62. PMID: 12502351

Ohmoto91: Ohmoto, T., Sakai, K., Hamada, N., Ohe, T. (1991). "Salicylic acid metabolism through a gentisate pathway by Pseudomonas sp TA-2." Agri. Biol. Chem. 55:1733-1737.

Poh80: Poh CL, Bayly RC (1980). "Evidence for isofunctional enzymes used in m-cresol and 2,5-xylenol degradation via the gentisate pathway in Pseudomonas alcaligenes." J Bacteriol 1980;143(1);59-69. PMID: 6995451

Qu11: Qu Y, Spain JC (2011). "Molecular and biochemical characterization of the 5-nitroanthranilic acid degradation pathway in Bradyrhizobium sp. strain JS329." J Bacteriol 193(12);3057-63. PMID: 21498645

Rabus02: Rabus R, Kube M, Beck A, Widdel F, Reinhardt R (2002). "Genes involved in the anaerobic degradation of ethylbenzene in a denitrifying bacterium, strain EbN1." Arch Microbiol 178(6);506-16. PMID: 12420173

Rani96: Rani M, Prakash D, Sobti RC, Jain RK (1996). "Plasmid-mediated degradation of o-phthalate and salicylate by a Moraxella sp." Biochem Biophys Res Commun 220(2);377-81. PMID: 8645313

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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