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/Assimilation → Aromatic Compounds Degradation → Phenolic Compounds Degradation|
Some taxa known to possess this pathway include : Haloferax sp. D1227
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
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
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
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
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
Moore02a: 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
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
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