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Enzyme Nomenclature
Information on EC 1.14.13.20 - 2,4-dichlorophenol 6-monooxygenase
for references in articles please use BRENDA:EC1.14.13.20
Word Map on EC 1.14.13.20
- 1.14.13.20
-
2,4-dichlorophenoxyacetic
-
chlorocatechols
- fad
- 3,5-dichlorocatechol
- chlorophenols
- eutrophus
- catechols
-
alcaligenes
-
bacteriol
- putida
-
2,4-d-degradative
- 3-chlorophenol
-
chloromuconate
- proteobacteria
-
non-substrate
-
hydroxylases
-
metagenome
-
alpha-2
-
ortho-substituted
-
polychlorinated
-
3-chloro
- 4-chlorocatechol
-
cycloisomerase
- acinetobacter
-
ralstonia
- maleylacetate
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.14.13.20
-
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RECOMMENDED NAME
GeneOntology No.
2,4-dichlorophenol 6-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2,4-dichlorophenol + NADPH + H+ + O2 = 3,5-dichlorocatechol + NADP+ + H2O
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
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-
-
-
reduction
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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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.
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CAS REGISTRY NUMBER
COMMENTARY
82047-82-3
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92767-55-0
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
containing the enzyme-encoding plasmid pJP4, genes tfdBI and tfdBII
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strains JMP222 and JMP134 containing the enzyme-encoding plasmid pJP4, genes tfdBI and tfdBII
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
-
the enzyme is involved in degradation of the herbicide 2,4-dichlorophenoxyacetic acid
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2,3-dichlorophenol + NADPH + O2
3,4-dichlorocatechol + NADP+ + H2O
Soil bacterium
-
113% of the activity with 2,4-dichlorophenol
-
-
?
2,5-dichlorophenol + NADPH + O2
3,6-dichlorocatechol + NADP+ + H2O
Soil bacterium
-
103% of the activity with 2,4-dichlorophenol
-
-
?
2,5-dichlorophenol + NADPH + O2
? + NADP+ + H2O
Soil bacterium
-
178% of the activity with 2,4-dichlorophenol
-
-
?
2-bromo-4-chlorophenol + NADPH + O2
3-bromo-5-chlorocatechol + NADP+ + H2O
Soil bacterium
-
82% of the activity with 2,4-dichlorophenol
-
-
?
2-chlorophenol + NADPH + O2
3-chlorocatechol + NADP+ + H2O
Soil bacterium
-
129% of the activity with 2,4-dichlorophenol
-
-
?
3-chlorophenol + NADPH + O2
4-chlorocatechol + NADP+ + H2O
Soil bacterium
-
230% of the activity with 2,4-dichlorophenol
-
-
?
4-bromo-2-chlorophenol + NADPH + O2
5-bromo-3-chlorocatechol + NADP+ + H2O
Soil bacterium
-
86% of the activity with 2,4-dichlorophenol
-
-
?
4-chloro-2-methylphenol + NADPH + O2
5-chloro-3-methylcatechol + NADP+ + H2O
Soil bacterium
-
95% of the activity with 2,4-dichlorophenol
-
-
?
2,3-dichlorophenol + NADPH + H+ + O2
? + NADP+ + H2O
26% activity compared to 2,4-dichlorophenol as substrate
-
-
?
2,3-dichlorophenol + NADPH + H+ + O2
? + NADP+ + H2O
26% activity compared to 2,4-dichlorophenol as substrate
-
-
?
2,4-dichlorophenol + NADPH + H+ + O2
3,5-dichlorocatechol + NADP+ + H2O
best substrate
-
-
?
2,4-dichlorophenol + NADPH + H+ + O2
3,5-dichlorocatechol + NADP+ + H2O
best substrate
-
-
?
2,4-dichlorophenol + NADPH + H+ + O2
3,5-dichlorocatechol + NADP+ + H2O
Soil bacterium
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
Proteobacteria S1
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-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
3,4-dichlorophenol + NADPH + H+ + O2
? + NADP+ + H2O
30% activity compared to 2,4-dichlorophenol as substrate
-
-
?
3,4-dichlorophenol + NADPH + H+ + O2
? + NADP+ + H2O
30% activity compared to 2,4-dichlorophenol as substrate
-
-
?
4-chlorophenol + NADPH + H+ + O2
? + NADP+ + H2O
68% activity compared to 2,4-dichlorophenol as substrate
-
-
?
4-chlorophenol + NADPH + H+ + O2
? + NADP+ + H2O
68% activity compared to 2,4-dichlorophenol as substrate
-
-
?
4-chlorophenol + NADPH + O2
5-chlorocatechol + NADP+ + H2O
-
-
-
-
?
additional information
?
-
-
pseudosubstrates evoke oxidation of NAD(P)H and oxygen consumption without themselves undergoing hydroxylation, the product is hydrogen peroxide: 2,5-dichlorophenol, 2,6-dichlorophenol, 3,4-dichlorophenol, 2, 4,5-trichlorophenol
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-
-
additional information
?
-
the enzyme shows a narrow substrate specificity with chlorophenols, 3,5-dichlorophenol is a poor substrate, overview
-
-
-
additional information
?
-
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the enzyme shows a narrow substrate specificity with chlorophenols, 3,5-dichlorophenol is a poor substrate, overview
-
-
-
additional information
?
-
the enzyme shows a narrow substrate specificity with chlorophenols, 3,5-dichlorophenol is a poor substrate, overview
-
-
-
additional information
?
-
-
the enzyme catabolizes 2,4-dichlorophenoxyacetate and 4-chloro-2-methylphenoxyacetate, using tfd functions carried on plasmid pJP4, tfdA cleaves the ether bonds of these herbicides to produce 2,4-dichlorophenol and 4-chloro-2-methylphenol, respectively, these intermediates can be degraded by two chlorophenol hydroxylases encoded by the tfdBI and tfdBII genes to produce the respective chlorocatechols, degradation pathway, a balance between chlorophenol-producing and chlorophenol-consuming reactions is necessary for growth on these compounds, overview
-
-
-
additional information
?
-
-
the enzyme catabolizes 2,4-dichlorophenoxyacetate and 4-chloro-2-methylphenoxyacetate, using tfd functions carried on plasmid pJP4, tfdA cleaves the ether bonds of these herbicides to produce 2,4-dichlorophenol and 4-chloro-2-methylphenol, respectively, these intermediates can be degraded by two chlorophenol hydroxylases encoded by the tfdBI and tfdBII genes to produce the respective chlorocatechols, degradation pathway, a balance between chlorophenol-producing and chlorophenol-consuming reactions is necessary for growth on these compounds, overview
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-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2,4-dichlorophenol + NADPH + H+ + O2
3,5-dichlorocatechol + NADP+ + H2O
A5LGH2
best substrate
-
-
?
2,4-dichlorophenol + NADPH + H+ + O2
3,5-dichlorocatechol + NADP+ + H2O
A5LGH2
best substrate
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
Proteobacteria S1
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
2,4-dichlorophenol + NADPH + O2
3,5-dichlorocatechol + NADP+ + H2O
-
-
-
-
?
4-chlorophenol + NADPH + O2
5-chlorocatechol + NADP+ + H2O
-
-
-
-
?
additional information
?
-
-
the enzyme catabolizes 2,4-dichlorophenoxyacetate and 4-chloro-2-methylphenoxyacetate, using tfd functions carried on plasmid pJP4, tfdA cleaves the ether bonds of these herbicides to produce 2,4-dichlorophenol and 4-chloro-2-methylphenol, respectively, these intermediates can be degraded by two chlorophenol hydroxylases encoded by the tfdBI and tfdBII genes to produce the respective chlorocatechols, degradation pathway, a balance between chlorophenol-producing and chlorophenol-consuming reactions is necessary for growth on these compounds, overview
-
-
-
additional information
?
-
-
the enzyme catabolizes 2,4-dichlorophenoxyacetate and 4-chloro-2-methylphenoxyacetate, using tfd functions carried on plasmid pJP4, tfdA cleaves the ether bonds of these herbicides to produce 2,4-dichlorophenol and 4-chloro-2-methylphenol, respectively, these intermediates can be degraded by two chlorophenol hydroxylases encoded by the tfdBI and tfdBII genes to produce the respective chlorocatechols, degradation pathway, a balance between chlorophenol-producing and chlorophenol-consuming reactions is necessary for growth on these compounds, overview
-
-
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FAD
-
1 mol of enzyme contains: 1.9 mol FAD; FAD cannot be replaced by riboflavin or FMN; flavoprotein
FAD
-
1 mol of enzyme contains: 4 mol FAD; flavoprotein; requires exogenous addition of FAD
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
KCl
-
high salt concentration inhibits, 0.05 M: 40%, 0.1 M: 50%, 0.2 M: 70%
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.6
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
30
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
tetramer
tetramer
-
alpha2beta2, 2 * 67000 + 2 * 45000, SDS-PAGE; alpha4, 4 * 66000, SDS-PAGE
-
tetramer
Proteobacteria S1
-
alpha4, 4 * 64000, SDS-PAGE
-
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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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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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
construction of tfdBI and tfdBII inactivation mutants on pJP4 plasmid, constructed in Escherichia coli strain BW25113 by allelic replacement of each of the genes tfdBI or tfdBII with a kanamycin resistance cassette, tfdBI and tfdBII are required for growth on 2,4-dichlorophenoxyacetate and 4-chloro-2-methylphenoxyacetate, with tfdBI contributing to a higher extent than tfdBII, phenotype, overview, accumulation of chlorophenol inhibits chlorophenoxyacetate degradation, and inactivation of the tfdB genes enhances the toxic effect of 2,4-dichlorophenoxyacetate on Cupriavidus necator cells
additional information
-
overexpression of tdfA inhibits chlorophenoxyacetate degradation in Burkholderia xenovorans/pJP4 cells
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.20)
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