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Enzyme Nomenclature
Information on EC 1.14.11.44 - (R)-dichlorprop dioxygenase (2-oxoglutarate)
for references in articles please use BRENDA:EC1.14.11.44
Word Map on EC 1.14.11.44
- 1.14.11.44
-
herbicide
-
aryloxyalkanoate
- maize
- corn
-
aryloxyphenoxypropionate
-
2,4-dichlorophenoxyacetic
-
agronomically
- accase
- ubiquitin
-
non-transgenic
- soybean
-
glyphosate-resistant
- glyphosate
-
near-isogenic
-
bacilliform
- rice
- sugarcane
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.14.11.44
-
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RECOMMENDED NAME
GeneOntology No.
(R)-dichlorprop dioxygenase (2-oxoglutarate)
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(R)-(2,4-dichlorophenoxy)propanoate + 2-oxoglutarate + O2 = 2,4-dichlorophenol + pyruvate + succinate + CO2
(2)
-
-
-
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2 = 4-chloro-2-methylphenol + pyruvate + succinate + CO2
(1)
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
((R)-2-(4-chloro-2-methylphenoxy)propanoate,2-oxoglutarate:oxygen oxidoreductase (pyruvate-forming)
Fe2+-dependent enzyme. The enzymes from the Gram-negative bacteria Delftia acidovorans MC1 and Sphingomonas herbicidovorans MH are involved in the degradation of the (R)-enantiomer of the phenoxyalkanoic acid herbicides mecoprop and dichlorprop [1,2].
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
-
the enzyme is involved in the degradation of phenoxyalkanoic acid herbicides in Sphingomonas herbicidovorans MH
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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
(R)-(2,4-dichlorophenoxy)propanoate + 2-oxoglutarate + O2
2,4-dichlorophenol + pyruvate + succinate + CO2
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
additional information
?
-
-
construction of homology models of SdpA and RdpA from Sphingomonas herbicidovorans MH and the use of docking to identify residues likely to be involved in herbicide binding
-
-
-
(R)-(2,4-dichlorophenoxy)propanoate + 2-oxoglutarate + O2
2,4-dichlorophenol + pyruvate + succinate + CO2
i.e. (R)-dichlorprop, the enzyme is involved in degrading the chiral herbicides (RS)-2-(2,4-dichlorophenoxy)propionate (dichlorprop) and (RS)-2-(4-chloro-2-methylphenoxy)propionate (mecoprop). RdpA is highly specific for the cleavage of the R-configuration of dichlorprop and mecoprop
-
-
?
(R)-(2,4-dichlorophenoxy)propanoate + 2-oxoglutarate + O2
2,4-dichlorophenol + pyruvate + succinate + CO2
i.e. (R)-dichlorprop, the enzyme is involved in degrading the chiral herbicides (RS)-2-(2,4-dichlorophenoxy)propionate (dichlorprop) and (RS)-2-(4-chloro-2-methylphenoxy)propionate (mecoprop). RdpA is highly specific for the cleavage of the R-configuration of dichlorprop and mecoprop
-
-
?
(R)-(2,4-dichlorophenoxy)propanoate + 2-oxoglutarate + O2
2,4-dichlorophenol + pyruvate + succinate + CO2
i.e. (R)-dichlorprop, the enzyme is involved in the degradation of phenoxyalkanoic acid herbicides in Sphingomonas herbicidovorans MH
-
-
?
(R)-(2,4-dichlorophenoxy)propanoate + 2-oxoglutarate + O2
2,4-dichlorophenol + pyruvate + succinate + CO2
-
the enzyme catalyzes the initial step of microbial degradation of the chiral herbicide (R,S)-2-(2,4-dichlorophenoxy)propionate (R,S-dichlorprop)
-
-
?
(R)-(2,4-dichlorophenoxy)propanoate + 2-oxoglutarate + O2
2,4-dichlorophenol + pyruvate + succinate + CO2
-
i.e. (R)-dichlorprop
-
-
?
(R)-(2,4-dichlorophenoxy)propanoate + 2-oxoglutarate + O2
2,4-dichlorophenol + pyruvate + succinate + CO2
i.e. (R)-dichlorprop. RdpA exclusively transforms the (R)-enantiomer of dichlorprop
-
-
?
(R)-(2,4-dichlorophenoxy)propanoate + 2-oxoglutarate + O2
2,4-dichlorophenol + pyruvate + succinate + CO2
-
i.e. (R)-dichlorprop. RdpA exclusively transforms the (R)-enantiomer of dichlorprop
-
-
?
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
i.e. (R)-mecoprop, the enzyme is involved in degrading the chiral herbicides (RS)-2-(2,4-dichlorophenoxy)propionate (dichlorprop) and (RS)-2-(4-chloro-2-methylphenoxy)propionate (mecoprop). RdpA is highly specific for the cleavage of the R-configuration of dichlorprop and mecoprop
-
-
?
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
i.e. (R)-mecoprop, the enzyme is involved in degrading the chiral herbicides (RS)-2-(2,4-dichlorophenoxy)propionate (dichlorprop) and (RS)-2-(4-chloro-2-methylphenoxy)propionate (mecoprop). RdpA is highly specific for the cleavage of the R-configuration of dichlorprop and mecoprop
-
-
?
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
-
-
-
-
?
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
i.e. (R)-mecoprop, the enzyme is involved in the degradation of phenoxyalkanoic acid herbicides in Sphingomonas herbicidovorans MH
-
-
?
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
-
i.e. (R)-mecoprop. RdpA exclusively transforms the (R)-enantiomer of mecoprop
-
-
?
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
i.e. (R)-mecoprop. RdpA exclusively transforms the (R)-enantiomer of mecoprop. The enzyme is specific for 2-oxoglutarate. Low levels of activity (1.9%) in presence of 2-oxoadipate. No activity with oxaloacetate, 2-oxobutyrate, and 2-oxovalerate
-
-
?
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
-
-
-
?
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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
(R)-(2,4-dichlorophenoxy)propanoate + 2-oxoglutarate + O2
2,4-dichlorophenol + pyruvate + succinate + CO2
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
(R)-(2,4-dichlorophenoxy)propanoate + 2-oxoglutarate + O2
2,4-dichlorophenol + pyruvate + succinate + CO2
P83310
i.e. (R)-dichlorprop, the enzyme is involved in degrading the chiral herbicides (RS)-2-(2,4-dichlorophenoxy)propionate (dichlorprop) and (RS)-2-(4-chloro-2-methylphenoxy)propionate (mecoprop). RdpA is highly specific for the cleavage of the R-configuration of dichlorprop and mecoprop
-
-
?
(R)-(2,4-dichlorophenoxy)propanoate + 2-oxoglutarate + O2
2,4-dichlorophenol + pyruvate + succinate + CO2
P83310
i.e. (R)-dichlorprop, the enzyme is involved in degrading the chiral herbicides (RS)-2-(2,4-dichlorophenoxy)propionate (dichlorprop) and (RS)-2-(4-chloro-2-methylphenoxy)propionate (mecoprop). RdpA is highly specific for the cleavage of the R-configuration of dichlorprop and mecoprop
-
-
?
(R)-(2,4-dichlorophenoxy)propanoate + 2-oxoglutarate + O2
2,4-dichlorophenol + pyruvate + succinate + CO2
Q8KSC8
i.e. (R)-dichlorprop, the enzyme is involved in the degradation of phenoxyalkanoic acid herbicides in Sphingomonas herbicidovorans MH
-
-
?
(R)-(2,4-dichlorophenoxy)propanoate + 2-oxoglutarate + O2
2,4-dichlorophenol + pyruvate + succinate + CO2
-
the enzyme catalyzes the initial step of microbial degradation of the chiral herbicide (R,S)-2-(2,4-dichlorophenoxy)propionate (R,S-dichlorprop)
-
-
?
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
P83310
i.e. (R)-mecoprop, the enzyme is involved in degrading the chiral herbicides (RS)-2-(2,4-dichlorophenoxy)propionate (dichlorprop) and (RS)-2-(4-chloro-2-methylphenoxy)propionate (mecoprop). RdpA is highly specific for the cleavage of the R-configuration of dichlorprop and mecoprop
-
-
?
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
P83310
i.e. (R)-mecoprop, the enzyme is involved in degrading the chiral herbicides (RS)-2-(2,4-dichlorophenoxy)propionate (dichlorprop) and (RS)-2-(4-chloro-2-methylphenoxy)propionate (mecoprop). RdpA is highly specific for the cleavage of the R-configuration of dichlorprop and mecoprop
-
-
?
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
-
-
-
-
?
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
Q8KSC8
i.e. (R)-mecoprop, the enzyme is involved in the degradation of phenoxyalkanoic acid herbicides in Sphingomonas herbicidovorans MH
-
-
?
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
Q8KSC8
-
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
-
ferrous iron is necessary for activity of the enzyme, and other divalent cations could not replace it
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(S)-2-(4-chloro-2-methylphenoxy)propanoate
-
Q93A variant retains 60% of wild-type enzyme activity, but this drops to 35% when the racemate is provided, suggesting that Gln93 prevents the incorrect enantiomer from binding to and inhibiting the enzyme
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
ascorbate
-
slightly reduced activity in the absence of ascorbate
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.108
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme F171A
0.38
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, wild-type enzyme
0.438
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme F171Q
1.55
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme R285A
2.3
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme V80A
2.8
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme Q93A
8.9
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme I106A
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.87
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme R285A
2.9
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme F171A
3.38
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme F171Q
4
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme I106A
4.13
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme V80A
4.2
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, wild-type enzyme
4.33
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme Q93A
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.45
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme I106A
0.56
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme R285A
1.55
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme Q93A
1.8
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme V80A
7.7
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme F171Q
11
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, wild-type enzyme
26.9
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C, mutant enzyme F171A
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6 - 7.5
-
pH 6.0: about 60% of maximal activity, pH 7.5: about 55% of maximal activity
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PDB
SCOP
CATH
ORGANISM
UNIPROT
Sphingobium herbicidovorans (strain ATCC 700291 / DSM 11019 / NBRC 16415 / MH)
Sphingobium herbicidovorans (strain ATCC 700291 / DSM 11019 / NBRC 16415 / MH)
Sphingobium herbicidovorans (strain ATCC 700291 / DSM 11019 / NBRC 16415 / MH)
Sphingobium herbicidovorans (strain ATCC 700291 / DSM 11019 / NBRC 16415 / MH)
Sphingobium herbicidovorans (strain ATCC 700291 / DSM 11019 / NBRC 16415 / MH)
Sphingobium herbicidovorans (strain ATCC 700291 / DSM 11019 / NBRC 16415 / MH)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
36000
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
trimer
trimer
-
3 * 34900, calculated from sequence; 3 * 36000, SDs-PAGE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed as His6-tagged fusion protein from Escherichia coli BL21(DE3)(pLysS)
-
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
rdpA and sdpA gene expression is constitutive at a basal level but is induced in response to (R,S)-dichlorprop degradation under in situ conditions
-
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
F171A
-
exhibits about 70% of wild-type enzyme activity with (R)-2-(4-chloro-2-methylphenoxy)propanoate. kcat/Km is 245% compared to the wild-type value
F171Q
-
exhibits about 70% of wild-type enzyme activity with (R)-2-(4-chloro-2-methylphenoxy)propanoate. kcat/Km is 70% compared to the wild-type value
I106A
-
exhibits about 30% of wild-type enzyme activity with (R)-2-(4-chloro-2-methylphenoxy)propanoate. kcat/Km is 5% compared to the wild-type value
I106G/G107I
-
exhibits 0.7% of wild-type enzyme activity with (R)-2-(4-chloro-2-methylphenoxy)propanoate
I106G/G107N
-
exhibits 8.7% of wild-type enzyme activity with (R)-2-(4-chloro-2-methylphenoxy)propanoate
L83A
-
exhibits about 10% of wild-type enzyme activity with (R)-2-(4-chloro-2-methylphenoxy)propanoate
Q93A
-
exhibits about 60% of wild-type enzyme activity with (R)-2-(4-chloro-2-methylphenoxy)propanoate. kcat/Km is 14% compared to the wild-type value
R285A
-
exhibits 14.8% of wild-type enzyme activity with (R)-2-(4-chloro-2-methylphenoxy)propanoate. kcat/Km is 5% compared to the wild-type value; exhibits about 10% of wild-type enzyme activity with (R)-2-(4-chloro-2-methylphenoxy)propanoate
V80A
-
exhibits about 60% of wild-type enzyme activity with (R)-2-(4-chloro-2-methylphenoxy)propanoate. kcat/Km is 17% compared to the wild-type value
Y221A
-
exhibits 5.2% of wild-type enzyme activity with (R)-2-(4-chloro-2-methylphenoxy)propanoate; exhibits about 10% of wild-type enzyme activity with (R)-2-(4-chloro-2-methylphenoxy)propanoate
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.11.44)
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