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Information on EC 1.14.11.44 - (R)-dichlorprop dioxygenase (2-oxoglutarate) for references in articles please use BRENDA:EC1.14.11.44
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EC Tree
IUBMB Comments 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].
The enzyme appears in viruses and cellular organisms
Synonyms
aad-1, (r)-phenoxypropionate/alpha-ketoglutarate-dioxygenase, alpha-ketoglutarate-dependent (r)-dichlorprop dioxygenase,
more
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(R)-phenoxypropionate/alpha-ketoglutarate-dioxygenase
2-oxoglutarate-dependent (R)-dichlorprop dioxygenase
-
alpha-ketoglutarate-dependent (R)-dichlorprop dioxygenase
-
ariloxyalkanoate-dioxygenase-1
(R)-phenoxypropionate/alpha-ketoglutarate-dioxygenase
-
(R)-phenoxypropionate/alpha-ketoglutarate-dioxygenase
-
-
AAD-1
-
ariloxyalkanoate-dioxygenase-1
-
ariloxyalkanoate-dioxygenase-1
-
-
RdpA
-
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(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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((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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(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
?
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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
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-
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(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
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-
?
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
-
-
-
?
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(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)
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-
?
(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
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-
?
(R)-2-(4-chloro-2-methylphenoxy)propanoate + 2-oxoglutarate + O2
4-chloro-2-methylphenol + pyruvate + succinate + CO2
Q8KSC8
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-
?
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Fe2+
-
ferrous iron is necessary for activity of the enzyme, and other divalent cations could not replace it
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(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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ascorbate
-
slightly reduced activity in the absence of ascorbate
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0.164
(R)-(2,4-dichlorophenoxy)propanoate
-
pH 6.8, 30°C
0.099 - 8.9
(R)-2-(4-chloro-2-methylphenoxy)propanoate
0.003
2-oxoglutarate
-
pH 6.8, 30°C
0.099
(R)-2-(4-chloro-2-methylphenoxy)propanoate
-
pH 6.8, 30°C
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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0.87 - 4.33
(R)-2-(4-chloro-2-methylphenoxy)propanoate
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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0.45 - 26.9
(R)-2-(4-chloro-2-methylphenoxy)propanoate
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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6 - 7.5
-
pH 6.0: about 60% of maximal activity, pH 7.5: about 55% of maximal activity
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5.8 - 5.9
isoelectric focusing
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SwissProt
brenda
-
SwissProt
brenda
-
UniProt
brenda
-
UniProt
brenda
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physiological function
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the enzyme is involved in the degradation of phenoxyalkanoic acid herbicides in Sphingomonas herbicidovorans MH
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RDPA_DELAC
295
0
33213
Swiss-Prot
RDPA_DELAC
295
0
33213
Swiss-Prot
RDPA_SPHHM
Sphingobium herbicidovorans (strain ATCC 700291 / DSM 11019 / NBRC 16415 / MH)
295
0
33213
Swiss-Prot
A0A2S6U356_9PROT
290
0
32475
TrEMBL
A0A2S6SHI1_9PROT
276
0
32034
TrEMBL
A0A2S6TIY1_9PROT
280
0
31565
TrEMBL
A0A2R8C6L2_9RHOB
274
0
30177
TrEMBL
A0A2S6TJZ1_9PROT
289
0
32834
TrEMBL
A0A2S6Q683_9PROT
291
0
32786
TrEMBL
A0A2S6QNK7_9PROT
278
0
32304
TrEMBL
A0A2S6QDE5_9PROT
279
0
31795
TrEMBL
A0A143QLE8_9NOCA
250
0
27363
TrEMBL
A0A2R8A8Y9_9RHOB
282
0
32067
TrEMBL
A0A2S6XG69_9ACTN
290
0
32064
TrEMBL
A0A2S6U1Q5_9PROT
296
0
33092
TrEMBL
A0A220W4P9_9SPHN
278
0
30903
TrEMBL
A0A2S6T7G1_9PROT
255
0
29224
TrEMBL
A0A2S6Q6L3_9PROT
281
0
32450
TrEMBL
A0A2S6QEF0_9PROT
301
0
33945
TrEMBL
A0A161GGY2_RHOFA
250
0
27378
TrEMBL
A0A2S6UHL6_9PROT
278
0
31083
TrEMBL
A0A2S6U2I1_9PROT
231
0
25283
TrEMBL
A0A2S6U212_9PROT
283
0
31328
TrEMBL
A0A2S6TR69_9PROT
282
0
32028
TrEMBL
A0A2Z4UG69_9RHIZ
290
0
32401
TrEMBL
A0A2S6TE18_9PROT
282
0
31987
TrEMBL
A0A2P5VLK9_9PROT
279
0
31522
TrEMBL
A0A2S6QEL0_9PROT
294
0
33953
TrEMBL
A0A2S6T2S4_9PROT
276
0
32020
TrEMBL
A0A2S6QEF9_9PROT
282
0
31876
TrEMBL
A0A2S6U972_9PROT
246
0
27908
TrEMBL
A0A2S6SVT4_9PROT
280
0
32443
TrEMBL
A0A2S6USD6_9PROT
259
0
30074
TrEMBL
A0A2S6TQ80_9PROT
295
0
33174
TrEMBL
A0A2P2E6X3_9PROT
273
0
30431
TrEMBL
A0A2S6SJS8_9PROT
275
0
31807
TrEMBL
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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)
Sphingobium herbicidovorans (strain ATCC 700291 / DSM 11019 / NBRC 16415 / MH)
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34900
-
3 * 34900, calculated from sequence
36000
-
3 * 36000, SDs-PAGE
36000
3 * 36000, SDs-PAGE
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trimer
3 * 36000, SDs-PAGE
trimer
-
3 * 36000, SDs-PAGE
-
trimer
-
3 * 34900, calculated from sequence; 3 * 36000, SDs-PAGE
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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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22
-
stable for up to 7 days
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inactivated by several freezing and thawing cycles
-
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4°C, stable for up to 8 weeks
-
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-
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expressed as His6-tagged fusion protein from Escherichia coli BL21(DE3)(pLysS)
-
expression of rdpA in Delftia acidovorans
-
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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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Müller, T.A.; Fleischmann, T.; van der Meer, J.R.; Kohler, H.P.
Purification and characterization of two enantioselective alpha-ketoglutarate-dependent dioxygenases, RdpA and SdpA, from Sphingomonas herbicidovorans MH
Appl. Environ. Microbiol.
72
4853-4861
2006
Sphingobium herbicidovorans (Q8KSC8), Sphingobium herbicidovorans
brenda
Paulin, M.M.; Nicolaisen, M.H.; Sorensen, J.
Abundance and expression of enantioselective rdpA and sdpA dioxygenase genes during degradation of the racemic herbicide (R,S)-2-(2,4-dichlorophenoxy)propionate in soil
Appl. Environ. Microbiol.
76
2873-2883
2010
Sphingobium herbicidovorans (Q8KSC8)
brenda
Westendorf, A.; Benndorf, D.; Müller, R.H.; Babel, W.
The two enantiospecific dichlorprop/alpha-ketoglutarate-dioxygenases from Delftia acidovorans MC1 - protein and sequence data of RdpA and SdpA
Microbiol. Res.
157
317-322
2002
Delftia acidovorans, Delftia acidovorans (P83310), Delftia acidovorans MC1, Delftia acidovorans MC1 (P83310)
brenda
Müller, T.A.; Zavodszky, M.I.; Feig, M.; Kuhn, L.A.; Hausinger, R.P.
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