Information on EC 1.14.13.20 - 2,4-dichlorophenol 6-monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.13.20
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RECOMMENDED NAME
GeneOntology No.
2,4-dichlorophenol 6-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2,4-dichlorophenol + NADPH + H+ + O2 = 3,5-dichlorocatechol + NADP+ + H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
2,4-dichlorophenoxyacetate degradation
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4-chloro-2-methylphenoxyacetate degradation
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Chlorocyclohexane and chlorobenzene degradation
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Metabolic pathways
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
2,4-dichlorophenol,NADPH:oxygen oxidoreductase (6-hydroxylating)
A flavoprotein (FAD). Also acts, more slowly, on 4-chlorophenol and 4-chloro-2-methylphenol; NADH can act instead of NADPH, but more slowly.
CAS REGISTRY NUMBER
COMMENTARY hide
82047-82-3
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92767-55-0
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
gene tfdBa
A5LGH2
UniProt
Manually annotated by BRENDA team
gene tfdBa
A5LGH2
UniProt
Manually annotated by BRENDA team
TFD6
-
-
Manually annotated by BRENDA team
RASC; TFD2
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Manually annotated by BRENDA team
RASC
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Manually annotated by BRENDA team
TFD2
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Manually annotated by BRENDA team
containing the enzyme-encoding plasmid pJP4, genes tfdBI and tfdBII
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Manually annotated by BRENDA team
S1
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Manually annotated by BRENDA team
Proteobacteria S1
S1
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Manually annotated by BRENDA team
PaW85
-
-
Manually annotated by BRENDA team
PaW85
-
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Manually annotated by BRENDA team
B6-9; TFD23
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Manually annotated by BRENDA team
Soil bacterium
metagenome constructed from polychlorinated biphenyl-contaminated soil
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Manually annotated by BRENDA team
B6-10; B6-5; EML146; TFD44
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Manually annotated by BRENDA team
B6-10
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Manually annotated by BRENDA team
B6-5
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Manually annotated by BRENDA team
EML146
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Manually annotated by BRENDA team
TFD44
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Manually annotated by BRENDA team
2811P
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
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the enzyme is involved in degradation of the herbicide 2,4-dichlorophenoxyacetic acid
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2,3-dichlorophenol + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
2,3-dichlorophenol + NADPH + O2
3,4-dichlorocatechol + NADP+ + H2O
show the reaction diagram
Soil bacterium
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113% of the activity with 2,4-dichlorophenol
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?
2,3-dichlorophenol + NADPH + O2
?
show the reaction diagram
2,4,5-trichlorophenol + NADPH + O2
?
show the reaction diagram
2,4,6-trichlorophenol + NADPH + O2
?
show the reaction diagram
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-
-
-
?
2,4-dibromophenol + NADPH + O2
?
show the reaction diagram
2,4-dichlorophenol + NADPH + H+ + O2
3,5-dichlorocatechol + NADP+ + H2O
show the reaction diagram
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
show the reaction diagram
2,5-dichlorophenol + NADPH + O2
3,6-dichlorocatechol + NADP+ + H2O
show the reaction diagram
Soil bacterium
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103% of the activity with 2,4-dichlorophenol
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?
2,5-dichlorophenol + NADPH + O2
?
show the reaction diagram
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-
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?
2,5-dichlorophenol + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
Soil bacterium
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178% of the activity with 2,4-dichlorophenol
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-
?
2,6-dichlorophenol + NADPH + O2
?
show the reaction diagram
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?
2-bromo-4-chlorophenol + NADPH + O2
3-bromo-5-chlorocatechol + NADP+ + H2O
show the reaction diagram
Soil bacterium
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82% of the activity with 2,4-dichlorophenol
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?
2-chloro-4-nitrophenol + NADPH + O2
?
show the reaction diagram
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?
2-chlorophenol + NADPH + O2
3-chlorocatechol + NADP+ + H2O
show the reaction diagram
Soil bacterium
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129% of the activity with 2,4-dichlorophenol
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?
2-chlorophenol + NADPH + O2
?
show the reaction diagram
2-cresol + NADPH + O2
?
show the reaction diagram
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incompletely metabolized
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?
2-methylphenol + NADPH + O2
?
show the reaction diagram
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?
3,4-dichlorophenol + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
3,4-dichlorophenol + NADPH + O2
?
show the reaction diagram
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?
3,5-dichlorophenol + NADPH + O2
?
show the reaction diagram
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?
3-chlorophenol + NADPH + O2
4-chlorocatechol + NADP+ + H2O
show the reaction diagram
Soil bacterium
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230% of the activity with 2,4-dichlorophenol
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?
3-chlorophenol + NADPH + O2
?
show the reaction diagram
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?
4-bromo-2-chlorophenol + NADPH + O2
5-bromo-3-chlorocatechol + NADP+ + H2O
show the reaction diagram
Soil bacterium
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86% of the activity with 2,4-dichlorophenol
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?
4-bromophenol + NADPH + O2
?
show the reaction diagram
4-chloro-2-methylphenol + NADPH + O2
5-chloro-3-methylcatechol + NADP+ + H2O
show the reaction diagram
Soil bacterium
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95% of the activity with 2,4-dichlorophenol
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?
4-chloro-2-methylphenol + NADPH + O2
?
show the reaction diagram
4-chloro-2-nitrophenol + NADPH + O2
?
show the reaction diagram
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?
4-chlorophenol + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
4-chlorophenol + NADPH + O2
5-chlorocatechol + NADP+ + H2O
show the reaction diagram
4-chlorophenol + NADPH + O2
?
show the reaction diagram
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2,4-dichlorophenol + NADPH + H+ + O2
3,5-dichlorocatechol + NADP+ + H2O
show the reaction diagram
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
show the reaction diagram
4-chloro-2-methylphenol + NADPH + O2
?
show the reaction diagram
4-chlorophenol + NADPH + O2
5-chlorocatechol + NADP+ + H2O
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
Soil bacterium
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0.1 mM, 130% of initial activity
Co2+
Soil bacterium
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0.1 mM, 110% of initial activity
Mn2+
Soil bacterium
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0.1 mM, 121% of initial activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2,4,5-Trichlorophenol
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2,4,6-Trichlorophenol
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2,4-Dichlorophenol
AgNO3
Cu2+
Soil bacterium
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0.1 mM, complete loss of activity
CuSO4
diethyldithiocarbamate
Dithionitrobenzoate
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dithiothreitol
FeSO4
guanidine hydrochloride
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KCl
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high salt concentration inhibits, 0.05 M: 40%, 0.1 M: 50%, 0.2 M: 70%
o-phenanthroline
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p-chloromercuribenzoate
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.002 - 0.014
2,4-Dichlorophenol
0.042 - 0.3
NADH
0.006 - 0.1
NADPH
0.057
O2
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additional information
additional information
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kinetics
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
6.83
2,4-Dichlorophenol
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
1.8
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without FAD
additional information
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in vivo degradation activities, overview
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.3 - 8
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phosphate buffer
7.5
Soil bacterium
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8.1 - 8.5
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100 mM Tris-HCl buffer
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45000
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alpha2beta2, 2 * 67000 + 2 * 45000, SDS-PAGE
63000
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alpha4, 4 * 63000, SDS-PAGE
64000
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alpha4, 4 * 64000, SDS-PAGE
66000
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alpha4, 4 * 66000, SDS-PAGE
67000
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alpha2beta2, 2 * 67000 + 2 * 45000, SDS-PAGE
69000
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alpha4, 4 * 69000, SDS-PAGE
224000
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ultracentrifugation
240000
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gel filtration
245000
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gel filtration
256000
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gel filtration, gradient PAGE
275000
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gel filtration and ultracentrifugation
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
tetramer
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
2,4-dichlorophenol, 0.1 mM, stabilizes during purification
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dithiothreitol, 1 mM, stabilizes during purification
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EDTA, 0.1 mM, stabilizes during purification
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FAD, 0.01 mM, stabilizes during purification
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 3 months stable
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
plasmid pJP4-encoded enzyme from Alcaligenes eutrophus JMP134 transferred to Pseudomonas putida 3CB5 and Alcaligenes eutrophus 335
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single step affinity chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
Soil bacterium
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expression in Pseudomonas putida
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gene tfdBa, DNA and amino acid sequence determination and analysis, phylogenetic analysis and tree, expression in Escherichia coli strain BL21, subcloning in Escherichia coli strains JM109 amd T7 Blue
A5LGH2;
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
Show AA Sequence (221 entries)
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