Catabolism of dl-α-phenylhydracrylic, phenylacetic and 3- and 4-hydroxyphenylacetic acid via homogentisic acid in a Flavobacterium sp.

Tweel, W.J.J. van den; Smits, JM Jan; Bont, J.A.M. de

doi:10.1007/bf00422006

Cited by 37 publications

(18 citation statements)

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“…Although the hydroxylase presents a broad substrate range, it might be classified as a 4-HPA hydroxylase, since plasmid pAJ221 was able to complement the 4-HPA-(unable to grow on 4-HPA) phenotype of E. coli W21, which has been characterized as a 4-HPA hydroxylasedeficient mutant of E. coli W (17). In addition to the 4-HPA hydroxylase of E. coli C (10), similar enzymes from other microorganisms have been described (4,24,30,42,43); however, each enzyme has a different substrate specificity. Interestingly, 4-HPA is also capable of hydroxylating chloroand methylaromatic compounds, which increases the potential for constructing microorganisms that can degrade environmental pollutants (34).…”

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confidence: 99%

Characterization of an Escherichia coli aromatic hydroxylase with a broad substrate range

1993

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confidence: 99%

Characterization of an Escherichia coli aromatic hydroxylase with a broad substrate range

1993

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“…Till recently, the bacterial pathway involved in aerobic PA metabolism was not clear. Although hydroxylated phenylacetic acids were detected in some PA degrading bacteria [8,9,11,12], neither ring-hydroxylating nor ring-cleaving reactions for PA metabolism could be demonstrated. Recently, PA 'aerobic hybrid pathway' via CoA-thioesters as intermediates has been reported in E. coli W and P. putida Y2 [22].…”

Section: Metabolism Of Phenylacetic Acid and 4-hydroxyphenylacetic Acidmentioning

confidence: 99%

“…In bacteria, metabolic pathways of PA assimilation have been widely studied and considered to follow either of four possible routes ( Figure 1). Utilization of PA via hydroxy intermediates (2-, 3-, or 4-hydroxyphenylacetic acid, Figure 1, route a, b or c, respectively) has been proposed in several microorganisms like Aspergillus, Nocardia, Flavobacterium, Trichosporon, Streptomyces, a chloridazon-degrading bacterium, P. putida, E. coli, Klebsiella, Acinetobacter and other unrelated microbes [6][7][8][9][10][11][12]. The metabolism of PA via hydroxylation of the aromatic ring was proposed in these strains.…”

Section: Introductionmentioning

confidence: 99%

“…The resulting intermediate (2,5-DHPA) yields maleylacetoacetic acid in subsequent steps. This ring cleaved structure ultimately results in the formation of acetoacetic acid and fumaric acid ( Figure 1, route e) [11,27,[29][30][31]. Other alternative pathways for 4-HPA metabolism have been reported (Figure 1, route f) in which degradation of the side-chain proceeds before oxidative ringcleavage occurs [5,32].…”

Section: Introductionmentioning

confidence: 99%

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Metabolism and Preferential Utilization of Phenylacetic acid and 4-Hydroxyphenylacetic Acid in Pseudomonas putida CSV86

Shrivastava¹,

Purohit²,

Phale³

2011

J Bioremed Biodegrad

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Metabolic pathways for phenylaceticacid (PA) and 4-hydroxyphenylacetic acid (4-HPA) from Pseudomonas putida CSV86 were elucidated. PA grown strain CSV86 cells showed higher oxygen-uptake on PA as compared to hydroxyphenylacetic acids. Detection of phenylacetyl-CoA ligase and absence of 4-hydroxyphenylacetic acid hydroxylase (4HPAH) and 3,4-dihydroxyphenylacetic acid-dioxygenase (3,4-DHPADO) activity supports this observation. 4-HPA grown cells showed oxygen-uptake on 4-HPA and 3,4-dihydroxyphenylacetic acid (3,4-DHPA) but showed significantly lower respiration rates on 2,5-dihydroxyphenylacetic acid and PA. Detection of 4HPAH and 3,4-DHPADO activities support the respiration data. Metabolic studies indicate that strain CSV86 metabolizes PA via phenylacetyl-CoA while 4-HPA via 3,4-DHPA pathway. Glucose grown cells showed lower activity of enzymes and respiration on PA, 4-HPA and 3,4-DHPA, suggesting that pathways are inducible. When grown on double carbon sources such as PA or 4-HPA plus glucose, CSV86 cells showed diauxic growth pattern with oxygen uptake on PA, 4-HPA and 3,4-DHPA in the first log-phase which was reduced during the second log-phase with increase in the respiration rate on glucose. This observation was supported by detection of high 4HPAH and 3,4-DHPADO activity in the first log-phase and glucose-6-phosphate dehydrogenase activity in the second log-phase. These results suggest that strain CSV86 utilizes PA and 4-HPA preferentially over glucose. Metabolism and Preferential Utilization of

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“…However, none of the possible routes which might be expected for phenylacetic acid catabolism by analogy to those of its hydroxy derivatives appears to operate in phenylacetate (PA)-degrading bacteria. The inability to demonstrate the hydroxylation of PA by cell extracts of different bacteria in the presence of different cofactors has been reported by several research groups (7,8,10,15,25,41,43). Therefore, there is still uncertainty about the aerobic pathway followed by bacteria for phenylacetic acid metabolism, which has to be considered unknown.…”

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Biochemical and Molecular Characterization of Phenylacetate-Coenzyme A Ligase, an Enzyme Catalyzing the First Step in Aerobic Metabolism of Phenylacetic Acid in Azoarcus evansii

Mohamed

2000

J Bacteriol

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Phenylacetate-coenzyme A ligase (PA-CoA ligase; AMP forming, EC 6.2.1.30), the enzyme catalyzing the first step in the aerobic degradation of phenylacetate (PA) in Azoarcus evansii, has been purified and characterized. The gene (paaK) coding for this enzyme was cloned and sequenced. The enzyme catalyzes the reaction of PA with CoA and MgATP to yield phenylacetyl-CoA (PACoA) plus AMP plus PPi. The enzyme was specifically induced after aerobic growth in a chemically defined medium containing PA or phenylalanine (Phe) as the sole carbon source. Growth with 4-hydroxyphenylacetate, benzoate, adipate, or acetate did not induce the synthesis of this enzyme. This enzymatic activity was detected very early in the exponential phase of growth, and a maximal specific activity of 76 nmol min ؊1 mg of cell protein ؊1 was measured. After 117-fold purification to homogeneity, a specific activity of 48 mol min ؊1 mg of protein Phenylacetic acid and its mono-or dihydroxylated derivatives are formed in nature from a wide variety of natural as well as synthetic compounds. Their microbial biodegradation and biotransformation have received the attention of many research groups for a long time. A number of bacteria and fungi have been isolated and studied to reveal the metabolic pathways of these acids under both aerobic and anaerobic growth conditions. Recently, the complete anaerobic metabolism of phenylacetic acid in the bacterium Thauera aromatica has been shown to follow a novel ␣-oxidation of the side chain of the coenzyme A (CoA)-activated acid, leading to the formation of the central intermediate benzoyl-CoA (Fig. 1). Further metabolism of benzoyl-CoA subsequently leads to the formation of three acetyl-CoA molecules and one CO 2 molecule (21,22,24,31,35,38,39).It has been established that the aerobic metabolism of most aromatic compounds starts by ring hydroxylation reactions carried out by mono-and dioxygenases. These oxic reactions, which are widely distributed in microorganisms, bring the aromatic rings of many aromatic compounds to the redox state present in catechol, protochatechuic and homoprotochatechuic acids, and gentisic and homogentisic acids. These compounds are considered common intermediates in the aerobic metabolism of most aromatic compounds (14,17).The aerobic metabolism of the hydroxylated derivatives of phenylacetic acid in many bacterial species follows this general pattern of oxic attack of the aromatic ring, leading to the formation of homogentisic acid (2,5-dihydroxyphenylactate) or homoprotocatechuic acid (3,4-dihydroxyphenylacetate) (4,5,12,13,28,34,41). However, none of the possible routes which might be expected for phenylacetic acid catabolism by analogy to those of its hydroxy derivatives appears to operate in phenylacetate (PA)-degrading bacteria. The inability to demonstrate the hydroxylation of PA by cell extracts of different bacteria in the presence of different cofactors has been reported by several research groups (7,8,10,15,25,41,43). Therefore, there is still uncertainty about the aerobic ...

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Catabolism of dl-α-phenylhydracrylic, phenylacetic and 3- and 4-hydroxyphenylacetic acid via homogentisic acid in a Flavobacterium sp.

Cited by 37 publications

References 19 publications

Characterization of an Escherichia coli aromatic hydroxylase with a broad substrate range

Characterization of an Escherichia coli aromatic hydroxylase with a broad substrate range

Metabolism and Preferential Utilization of Phenylacetic acid and 4-Hydroxyphenylacetic Acid in Pseudomonas putida CSV86

Biochemical and Molecular Characterization of Phenylacetate-Coenzyme A Ligase, an Enzyme Catalyzing the First Step in Aerobic Metabolism of Phenylacetic Acid in Azoarcus evansii

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