BRENDA - Enzyme Database
show all sequences of 1.13.11.66

Substrate specificity of Sphingobium chlorophenolicum 2,6-dichlorohydroquinone 1,2-dioxygenase

Machonkin, T.E.; Doerner, A.E.; Biochemistry 50, 8899-8913 (2011)

Data extracted from this reference:

Inhibitors
Inhibitors
Commentary
Organism
Structure
2,6-dibromophenol
competitive
Sphingobium chlorophenolicum
3-bromocatechol
inactivation
Sphingobium chlorophenolicum
ortho-disubstituted phenols
-
Sphingobium chlorophenolicum
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.0013
-
2,6-dibromohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
0.0032
-
2,6-dichlorohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
0.0044
-
2-chloro-6-methylhydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
0.0085
-
bromohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
0.01
-
chlorohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
0.021
-
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,2-cleavage, pH 7.0, 23°C
Sphingobium chlorophenolicum
0.041
-
methylhydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
0.055
-
2,6-dimethylhydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
0.07
-
O2
cosubstrate 2,6-dimethylhydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
0.12
-
O2
cosubstrate 2,6-dibromohydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
0.19
-
O2
cosubstrate 2,6-dichlorohydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
0.26
-
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,6-cleavage, pH 7.0, 23°C
Sphingobium chlorophenolicum
Organism
Organism
UniProt
Commentary
Textmining
Sphingobium chlorophenolicum
Q9ZBB0
-
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
2,6-dibromohydroquinone + O2
-
718916
Sphingobium chlorophenolicum
2-bromomaleylacetate + Br-
-
-
-
?
2,6-dichlorohydroquinone + O2
complete conversion of substrate
718916
Sphingobium chlorophenolicum
2-chloromaleylacetate + Cl-
-
-
-
?
2,6-dimethylhydroquinone + O2
-
718916
Sphingobium chlorophenolicum
2-methylmaleylacetone + ?
-
-
-
?
2-chloro-6-methylhydroquinone
-
718916
Sphingobium chlorophenolicum
?
complete conversion of substrate, yields a mixture of 1,2- and 1,6-cleavage products. The two modes of cleavage have different Km values for oxygen, consistent with a mechanism in which the substrate binds in two catalytically productive orientations
-
-
?
bromohydroquinone + O2
-
718916
Sphingobium chlorophenolicum
maleylacetate + Br-
-
-
-
?
chlorohydroquinone + O2
-
718916
Sphingobium chlorophenolicum
maleylacetate + Cl-
-
-
-
?
methylhydroquinone + O2
-
718916
Sphingobium chlorophenolicum
maleylacetone + ?
-
-
-
?
additional information
exhibits a high degree of substrate specificity for 2,6-disubstituted hydroquinones, with halogens greatly preferred at those positions. The asymmetric substrate 2-chloro-6-methylhydroquinone yields a mixture of 87% 1,2-cleavage and 13% 1,6-cleavage products with different Km values for oxygen, consistent with a mechanism in which the substrate binds in two catalytically productive orientations. Monosubstituted hydroquinones show a limited amount of ring cleavage but rapidly inactivate the enzyme in an O2-dependent fashion, suggesting that oxidation of the Fe(II) may be the cause
718916
Sphingobium chlorophenolicum
?
-
-
-
?
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
1.25
-
2,6-dimethylhydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
1.4
-
O2
cosubstrate 2,6-dimethylhydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
1.6
-
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,2-cleavage, pH 7.0, 23°C
Sphingobium chlorophenolicum
1.61
-
2,6-dibromohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
1.8
-
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,6-cleavage, pH 7.0, 23°C
Sphingobium chlorophenolicum
2.2
-
O2
cosubstrate 2,6-dibromohydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
2.41
-
2-chloro-6-methylhydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
3.05
-
2,6-dichlorohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
4.8
-
O2
cosubstrate 2,6-dichlorohydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
2,6-dibromophenol
competitive
Sphingobium chlorophenolicum
3-bromocatechol
inactivation
Sphingobium chlorophenolicum
ortho-disubstituted phenols
-
Sphingobium chlorophenolicum
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
0.0013
-
2,6-dibromohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
0.0032
-
2,6-dichlorohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
0.0044
-
2-chloro-6-methylhydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
0.0085
-
bromohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
0.01
-
chlorohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
0.021
-
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,2-cleavage, pH 7.0, 23°C
Sphingobium chlorophenolicum
0.041
-
methylhydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
0.055
-
2,6-dimethylhydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
0.07
-
O2
cosubstrate 2,6-dimethylhydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
0.12
-
O2
cosubstrate 2,6-dibromohydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
0.19
-
O2
cosubstrate 2,6-dichlorohydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
0.26
-
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,6-cleavage, pH 7.0, 23°C
Sphingobium chlorophenolicum
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
2,6-dibromohydroquinone + O2
-
718916
Sphingobium chlorophenolicum
2-bromomaleylacetate + Br-
-
-
-
?
2,6-dichlorohydroquinone + O2
complete conversion of substrate
718916
Sphingobium chlorophenolicum
2-chloromaleylacetate + Cl-
-
-
-
?
2,6-dimethylhydroquinone + O2
-
718916
Sphingobium chlorophenolicum
2-methylmaleylacetone + ?
-
-
-
?
2-chloro-6-methylhydroquinone
-
718916
Sphingobium chlorophenolicum
?
complete conversion of substrate, yields a mixture of 1,2- and 1,6-cleavage products. The two modes of cleavage have different Km values for oxygen, consistent with a mechanism in which the substrate binds in two catalytically productive orientations
-
-
?
bromohydroquinone + O2
-
718916
Sphingobium chlorophenolicum
maleylacetate + Br-
-
-
-
?
chlorohydroquinone + O2
-
718916
Sphingobium chlorophenolicum
maleylacetate + Cl-
-
-
-
?
methylhydroquinone + O2
-
718916
Sphingobium chlorophenolicum
maleylacetone + ?
-
-
-
?
additional information
exhibits a high degree of substrate specificity for 2,6-disubstituted hydroquinones, with halogens greatly preferred at those positions. The asymmetric substrate 2-chloro-6-methylhydroquinone yields a mixture of 87% 1,2-cleavage and 13% 1,6-cleavage products with different Km values for oxygen, consistent with a mechanism in which the substrate binds in two catalytically productive orientations. Monosubstituted hydroquinones show a limited amount of ring cleavage but rapidly inactivate the enzyme in an O2-dependent fashion, suggesting that oxidation of the Fe(II) may be the cause
718916
Sphingobium chlorophenolicum
?
-
-
-
?
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
1.25
-
2,6-dimethylhydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
1.4
-
O2
cosubstrate 2,6-dimethylhydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
1.6
-
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,2-cleavage, pH 7.0, 23°C
Sphingobium chlorophenolicum
1.61
-
2,6-dibromohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
1.8
-
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,6-cleavage, pH 7.0, 23°C
Sphingobium chlorophenolicum
2.2
-
O2
cosubstrate 2,6-dibromohydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
2.41
-
2-chloro-6-methylhydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
3.05
-
2,6-dichlorohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
4.8
-
O2
cosubstrate 2,6-dichlorohydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
KCat/KM [mM/s]
kcat/KM Value [1/mMs-1]
kcat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
0.7
-
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,6-cleavage, pH 7.0, 23°C
Sphingobium chlorophenolicum
7
-
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,2-cleavage, pH 7.0, 23°C
Sphingobium chlorophenolicum
19
-
O2
cosubstrate 2,6-dibromohydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
20
-
O2
cosubstrate 2,6-dimethylhydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
23
-
2,6-dimethylhydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
26
-
O2
cosubstrate 2,6-dichlorohydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
540
-
2-chloro-6-methylhydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
1000
-
2,6-dichlorohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
1200
-
2,6-dibromohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
KCat/KM [mM/s] (protein specific)
KCat/KM Value [1/mMs-1]
KCat/KM Value Maximum [1/mMs-1]
Substrate
Commentary
Organism
Structure
0.7
-
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,6-cleavage, pH 7.0, 23°C
Sphingobium chlorophenolicum
7
-
O2
cosubstrate 2-chloro-6-methylhydroquinone, 1,2-cleavage, pH 7.0, 23°C
Sphingobium chlorophenolicum
19
-
O2
cosubstrate 2,6-dibromohydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
20
-
O2
cosubstrate 2,6-dimethylhydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
23
-
2,6-dimethylhydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
26
-
O2
cosubstrate 2,6-dichlorohydroquinone, pH 7.0, 23°C
Sphingobium chlorophenolicum
540
-
2-chloro-6-methylhydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
1000
-
2,6-dichlorohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
1200
-
2,6-dibromohydroquinone
pH 7.0, 23°C
Sphingobium chlorophenolicum
Other publictions for EC 1.13.11.66
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Synonyms
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
744430
Ferraroni
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2
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1
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9
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2
2
1
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3
3
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1
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6
-
13
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1
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11
1
3
1
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11
1
1
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1
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1
1
1
1
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719179
Zhang
Identification of the para-nit ...
Pseudomonas sp.
BMC Microbiol.
12
27
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1
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1
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8
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1
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1
1
1
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1
1
2
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1
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2
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1
1
1
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1
1
2
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718555
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Sphingomonas sp., Sphingomonas sp. TTNP3
AMB Express
1
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-
-
-
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9
2
-
1
6
-
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9
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2
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2
-
32
2
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2
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2
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18
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2
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1
6
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2
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2
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32
2
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2
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2
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2
2
718916
Machonkin
Substrate specificity of Sphin ...
Sphingobium chlorophenolicum
Biochemistry
50
8899-8913
2011
-
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3
12
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1
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9
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3
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12
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8
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9
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9
9
719104
Shen
Cloning and characterization o ...
Pseudomonas putida, Pseudomonas putida DLL-E4
Biores. Technol.
101
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-
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2
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2
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7
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4
2
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719327
Yin
Characterization of MnpC, a hy ...
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Curr. Microbiol.
61
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2010
-
-
1
-
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1
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2
1
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28
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1
3
4
1
1
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1
1
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1
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1
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1
3
4
1
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1
1
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720066
Machonkin
Determination of the active si ...
Sphingobium chlorophenolicum
J. Biol. Inorg. Chem.
15
291-301
2010
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1
1
5
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1
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1
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1
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5
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1
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719714
Moonen
Hydroquinone dioxygenase from ...
Pseudomonas fluorescens, Pseudomonas fluorescens ACB
J. Bacteriol.
190
5199-5209
2008
1
-
-
-
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12
1
-
1
3
-
-
13
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1
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1
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14
1
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1
1
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1
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1
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12
1
1
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1
3
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1
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1
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14
1
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1
1
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718727
Xun
Characterization of 2,6-dichlo ...
Sphingobium chlorophenolicum
Biochem. Biophys. Res. Commun.
266
322-325
1999
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718831
Xu
Evidence that pcpA encodes 2,6 ...
Sphingobium chlorophenolicum
Biochemistry
38
7659-7669
1999
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719693
Miyauchi
Cloning and sequencing of a no ...
Sphingomonas paucimobilis
J. Bacteriol.
181
6712-6719
1999
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