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EC Tree
IUBMB Comments Also acts on 4-nitrophenyl esters, with optimum chain-length C6 to C8.
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
dehp esterase,
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esterase, bis(2-ethylhexyl) phthalate
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bis(2-ethylhexyl)phthalate + H2O = 2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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hydrolysis of carboxylic ester
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bis(2-ethylhexyl)phthalate acylhydrolase
Also acts on 4-nitrophenyl esters, with optimum chain-length C6 to C8.
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4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
4-nitrophenyl acylester + H2O
4-nitrophenol + carboxylic acid
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with optimum chain-length C6 to C8, cleavage of bis(2-ethylhexyl)phthalate is 10000times slower than cleavage of 4-nitrophenyl octanoate
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4-nitrophenyl butanoate + H2O
4-nitrophenol + butanoate
4-nitrophenyl octanoate + H2O
4-nitrophenol + octanoate
benzylbutylphthalate + H2O
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bis(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
di(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
dibutylphthalate + H2O
butylphthalate + butanol
diethylphthalate + H2O
ethylphthalate + ethanol
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dimethylphthalate + H2O
methylphthalate + methanol
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dipentylphthalate + H2O
pentylphthalate + pentanol
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4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
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4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
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4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
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4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
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4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
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4-nitrophenyl butanoate + H2O
4-nitrophenol + butanoate
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4-nitrophenyl butanoate + H2O
4-nitrophenol + butanoate
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4-nitrophenyl octanoate + H2O
4-nitrophenol + octanoate
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4-nitrophenyl octanoate + H2O
4-nitrophenol + octanoate
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benzylbutylphthalate + H2O
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benzylbutylphthalate + H2O
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bis(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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bis(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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bis(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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bis(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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bis(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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bis(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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bis(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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bis(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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bis(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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di(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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di(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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dibutylphthalate + H2O
butylphthalate + butanol
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dibutylphthalate + H2O
butylphthalate + butanol
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bis(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
bis(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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bis(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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bis(2-ethylhexyl)phthalate + H2O
2-ethylhexyl phthalate + 2-ethylhexan-1-ol
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Cu2+
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1 mM, 127% of initial activity
Fe3+
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1 mM, 162% of initial activity
Mn2+
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0.25 mM, maximum esterase activity
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4-mercuribenzoate
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complete inhibition at 1 mM, 80% inhibition at 0.1 mM
4-nitrophenyl phosphate
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4-nitrophenyl-diethyl phosphate
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synonym: Paraoxon, complete inhibition at 0.1 and 1 mM
Ca2+
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1 mM, 45.5% residual activity
diisopropylfluorophosphate
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complete inhibition at 1 mM, 80% inhibition at 0.1 mM
Dimethylsulfoxide
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70% inihibition at 5%
dodecyl beta-maltoside
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eserine
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complete inhibition at 1 mM, 80% inhibition at 0.1 mM
ethyleneglycolmonomethyl ether
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70% inihibition at 5%
HgCl2
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complete inhibition at 1 mM, 80% inhibition at 0.1 mM
K+
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1 mM, 55.8% residual activity
Mg2+
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1 mM, 15.4% residual activity
Na+
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1 mM, 54.3% residual activity
phenylmethylsulfonyl fluoride
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75% inhibition at 1 mM
Zn2+
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1 mM, 21.5% residual activity
additional information
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cleavage of bis(2-ethylhexyl)phthalate is strongly inhibited by a wheat cell wall and by a triglyceride preparation, cleavage of the water-soluble substrate, 4-nitrophenylacetate is not inhibited
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1.308
4-nitrophenyl acetate
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50°C, pH 8.0
0.005
bis(2-ethylhexyl)phthalate
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30°C
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0.0000833
bis(2-ethylhexyl)phthalate
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89.5
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substrate 4-nitrophenyl acetate, pH 50°C, pH 8.0
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rapid loss of activity above
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9.1
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calculated from sequence
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var. Kolibri
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wheat
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additional information
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enzyme activity in human intestine is 2.4fold higher than that in human liver
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additional information
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enzyme activity in rat intestine is 1.7fold less than that in rat liver
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higher enzyme activity compared to cytosol
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evolution
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an esterase-mediated pathway in rat liver might occur predominantly rather than in human liver although it is comparable between human and rat
evolution
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an esterase-mediated pathway in rat liver might occur predominantly rather than in human liver although it is comparable between human and rat
metabolism
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an esterase-mediated pathway in rat liver might occur predominantly rather than in human liver although it is comparable between human and rat
metabolism
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an esterase-mediated pathway in rat liver might occur predominantly rather than in human liver although it is comparable between human and rat
physiological function
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strains grows in mineral salt medium containing dimethyl phthalate, diethyl phthalate, di-n-butyl phthalate, and di-(2-ethylhexyl) phthalate. The consumption of dimethyl phthalate, diethyl phthalate, di-n-butyl phthalate is up to 98.87%, 94.94%, and 72.15%, respectively
physiological function
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the bis(2-ethylhexyl)phthalate biodegradation pathway appears to proceed by enzymatic ester hydrolysis of bis(2-ethylhexyl)phthalate with the formation of mono(2-ethylhexyl) phthalate. Final product of the pathway is 2,3-butanediol
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22000
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x * 22000, SDS-PAGE
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x * 53000, SDS-PAGE
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x * 53000, SDS-PAGE
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x * 40340, calculated from sequence, x * 40000, SDS-PAGE
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dimethyl sulfoxide
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high activity in the presence of 10% v/v
Methanol
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high activity in the presence of 10% v/v
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4°C, half-life: 1 week for the enzyme from first steps of purification, 1 day for the enzyme from last steps of purification and purified enzyme
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expression in Escherichia coli
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degradation
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di(2-ethylhexyl) phthalate, dibutyl phthalate, benzyl butyl phthalate and dipentyl phthalate can be almost completely degraded within four days in mineral salt medium under shaking conditions. 5.9% of the dimethyl phthalate and 42.9% of the diethyl phthalate present, are degraded under the same conditions. At temperatures of 10-50°C, strain B1811 is able to grow and utilize all the phthalate esters except for dimethylphthalate
degradation
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Fusarium culmorum degrades 95% of 1000 mg/l di(2-ethylhexyl) phthalate within 60 h of growth. Di(2-ethylhexyl) phthalate is fully metabolized wth butanediol as the final product
degradation
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di(2-ethylhexyl) phthalate, dibutyl phthalate, benzyl butyl phthalate and dipentyl phthalate can be almost completely degraded within four days in mineral salt medium under shaking conditions. 5.9% of the dimethyl phthalate and 42.9% of the diethyl phthalate present, are degraded under the same conditions. At temperatures of 10-50°C, strain B1811 is able to grow and utilize all the phthalate esters except for dimethylphthalate
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synthesis
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optimum conditions for the production of the maximum (30.5 U) intracellular esterase, are 10 mM di(2-ethylhexyl)phthalate and 72 h incubation at pH 8.0 were found as optimum conditions
synthesis
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optimum conditions for the production of the maximum (30.5 U) intracellular esterase, are 10 mM di(2-ethylhexyl)phthalate and 72 h incubation at pH 8.0 were found as optimum conditions
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Krell, H.W.; Sandermann, H.
Plant biochemistry of xenobiotics. Purification and properties of a wheat esterase hydrolyzing the plasticizer chemical, bis(2-ethylhexyl)phthalate
Eur. J. Biochem.
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57-62
1984
Triticum aestivum
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Krell, H.W.; Sandermann, H.
Compartmentation of the plant metabolic enzymes for the persistent plasticizer chemical, bis-2-(ethylhexyl)-phthalate
Plant Sci.
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87-93
1985
Triticum aestivum
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Krell, H.W.; Sandermann, H.
Metabolism of the persistent plasticizer chemical bis(2-ethylhexyl) phthalate in cell suspension cultures of wheat (Triticum aestivum L.). Discrepancy from the intact plant
J. Agric. Food Chem.
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194-198
1986
Triticum aestivum
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Choi, K.; Joo, H.; Campbell, J.L.; Andersen, M.E.; Clewell, H.J.
In vitro intestinal and hepatic metabolism of di(2-ethylhexyl) phthalate (DEHP) in human and rat
Toxicol. In Vitro
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1451-1457
2013
Homo sapiens, Rattus norvegicus
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Pradeep, S.; Josh, M.; Hareesh, E.; Kumar, S.; Benjamin, S.
Achromobacter denitrificans strain SP1 produces an intracellular esterase upon utilizing di(2ethylhexyl)phthalate
Int. Biodeter. Biodegrad.
105
160-167
2015
Achromobacter denitrificans, Achromobacter denitrificans SP1
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Zhang, J.; Zhang, C.; Zhu, Y.; Li, J.; Li, X.
Biodegradation of seven phthalate esters by Bacillus mojavensis B1811
Int. Biodeter. Biodegrad.
132
200-207
2018
Bacillus mojavensis, Bacillus mojavensis B1811
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Fang, Y.; Zhang, L.; Wang, J.; Zhou, Y.; Ye, B.
Biodegradation of phthalate esters by a newly isolated Acinetobacter sp. strain LMB-5 and characteristics of its esterase
Pedosphere
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606-615
2017
Acinetobacter sp. LMB-5
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Ahuactzin-Perez, M.; Tlecuitl-Beristain, S.; Garcia-Davila, J.; Gonzalez-Perez, M.; Gutierrez-Ruiz, M.C.; Sanchez, C.
Degradation of di(2-ethyl hexyl) phthalate by Fusarium culmorum Kinetics, enzymatic activities and biodegradation pathway based on quantum chemical modeling pathway based on quantum chemical modeling
Sci. Total Environ.
566-567
1186-1193
2016
Fusarium culmorum
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