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
strain RD5-C2, gene tfdBa
UniProt
Manually annotated by BRENDA team
strain RD5-C2, gene tfdBa
UniProt
Manually annotated by BRENDA team
TFD6
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-
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
strain LB400 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
S1
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Manually annotated by BRENDA team
PaW85
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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
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
-
-
-
-
?
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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-
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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
?
-
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
Acinetobacter sp.
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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
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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