BRENDA - Enzyme Database
show all sequences of 3.8.1.7

Histidine 90 function in 4-chlorobenzoyl-coenzyme A dehalogenase catalysis

Zhang, W.; Wei, Y.; Luo, L.; Taylor, K.L.; Yang, G.; Dunaway-Mariano, D.; Benning, M.M.; Holden, H.M.; Biochemistry 40, 13474-13482 (2001)

Data extracted from this reference:

Crystallization (Commentary)
Crystallization
Organism
purified recombinant mutant H90Q complexed with the substrate, 8% PEG 8000, 0.2 M potassium chloride, 50 mM CHES, pH 9.0, 5 mM NaN3, 4 °C, X-ray diffraction structure determination and analysis at 1.8 A resolution
Pseudomonas sp.
Engineering
Amino acid exchange
Commentary
Organism
H90Q
site-directed mutagenesis, exchange of the active site H90, reduced formation of arylated enzyme intermediate, and 154fold reduction of arylated enzyme intermediate hydrolysis, active site structure
Pseudomonas sp.
KM Value [mM]
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
additional information
-
additional information
kinetics
Pseudomonas sp.
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
4-chlorobenzoyl-CoA + H2O
Pseudomonas sp.
-
4-hydroxybenzoyl-CoA + chloride
-
-
?
Organism
Organism
Primary Accession No. (UniProt)
Commentary
Textmining
Pseudomonas sp.
A5JTM5
-
-
Reaction
Reaction
Commentary
Organism
4-chlorobenzoyl-CoA + H2O = 4-hydroxybenzoyl CoA + chloride
specific for dehalogenation at the 4-position, can dehalogenate substrates bearing fluorine, chlorine, bromine and iodine in the 4-position, mechanism, attack of Asp145 on the C(4) of the substrates' benzoyl ring to form a Meisenheimer intermediate, followed by expulsion of chloride ion to form an arylated enzyme intermediate, and ester hydrolysis to form 4-hydroxybenzoyl-CoA, active site residue His90 is involved and important for the regeneration of the active enzyme
Pseudomonas sp.
Specific Activity [micromol/min/mg]
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
1.5
-
purified wild-type enzyme
Pseudomonas sp.
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
4-chlorobenzoyl-CoA + H2O
-
654585
Pseudomonas sp.
4-hydroxybenzoyl-CoA + chloride
-
-
-
?
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
25
-
assay at
Pseudomonas sp.
Turnover Number [1/s]
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
additional information
-
additional information
turnover rates for dormations of intermediates, wildtype and mutant
Pseudomonas sp.
0.0002
-
4-chlorobenzoyl-CoA
multiple turnovers, mutant H90Q, pH 7.5, 25°C
Pseudomonas sp.
0.016
-
4-chlorobenzoyl-CoA
single turnover, mutant H90Q, pH 7.5, 25°C
Pseudomonas sp.
0.7
-
4-chlorobenzoyl-CoA
multiple turnovers, wild-type enzyme, pH 7.5, 25°C
Pseudomonas sp.
2.3
-
4-chlorobenzoyl-CoA
single turnover, wild-type enzyme, pH 7.5, 25°C
Pseudomonas sp.
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
-
assay at
Pseudomonas sp.
Crystallization (Commentary) (protein specific)
Crystallization
Organism
purified recombinant mutant H90Q complexed with the substrate, 8% PEG 8000, 0.2 M potassium chloride, 50 mM CHES, pH 9.0, 5 mM NaN3, 4 °C, X-ray diffraction structure determination and analysis at 1.8 A resolution
Pseudomonas sp.
Engineering (protein specific)
Amino acid exchange
Commentary
Organism
H90Q
site-directed mutagenesis, exchange of the active site H90, reduced formation of arylated enzyme intermediate, and 154fold reduction of arylated enzyme intermediate hydrolysis, active site structure
Pseudomonas sp.
KM Value [mM] (protein specific)
KM Value [mM]
KM Value Maximum [mM]
Substrate
Commentary
Organism
Structure
additional information
-
additional information
kinetics
Pseudomonas sp.
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
4-chlorobenzoyl-CoA + H2O
Pseudomonas sp.
-
4-hydroxybenzoyl-CoA + chloride
-
-
?
Specific Activity [micromol/min/mg] (protein specific)
Specific Activity Minimum [µmol/min/mg]
Specific Activity Maximum [µmol/min/mg]
Commentary
Organism
1.5
-
purified wild-type enzyme
Pseudomonas sp.
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
4-chlorobenzoyl-CoA + H2O
-
654585
Pseudomonas sp.
4-hydroxybenzoyl-CoA + chloride
-
-
-
?
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
25
-
assay at
Pseudomonas sp.
Turnover Number [1/s] (protein specific)
Turnover Number Minimum [1/s]
Turnover Number Maximum [1/s]
Substrate
Commentary
Organism
Structure
additional information
-
additional information
turnover rates for dormations of intermediates, wildtype and mutant
Pseudomonas sp.
0.0002
-
4-chlorobenzoyl-CoA
multiple turnovers, mutant H90Q, pH 7.5, 25°C
Pseudomonas sp.
0.016
-
4-chlorobenzoyl-CoA
single turnover, mutant H90Q, pH 7.5, 25°C
Pseudomonas sp.
0.7
-
4-chlorobenzoyl-CoA
multiple turnovers, wild-type enzyme, pH 7.5, 25°C
Pseudomonas sp.
2.3
-
4-chlorobenzoyl-CoA
single turnover, wild-type enzyme, pH 7.5, 25°C
Pseudomonas sp.
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
7.5
-
assay at
Pseudomonas sp.
Other publictions for EC 3.8.1.7
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
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)
720401
Plotnikova
Degradation of 4-chlorobipheny ...
Rhodococcus ruber, Rhodococcus ruber P25
Microbiology
81
143-153
2012
-
-
1
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-
-
-
-
-
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2
-
2
-
-
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1
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4
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1
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-
2
-
-
-
-
-
1
-
-
4
-
-
-
-
-
-
-
-
-
-
1
1
-
-
-
719717
Wang
A novel hydrolytic dehalogenas ...
Pseudomonas sp., Pseudomonas sp. CTN-3
J. Bacteriol.
192
2737-2745
2010
-
-
1
-
7
-
6
1
-
2
1
2
-
3
-
-
1
-
-
-
-
2
6
1
1
-
3
1
1
-
1
1
-
1
-
-
-
1
1
-
7
-
-
6
-
1
-
2
1
2
-
-
-
1
-
-
-
2
6
1
1
-
3
1
1
-
1
1
-
1
1
-
1
1
685426
Zhou
Structure and denaturation of ...
Arthrobacter sp.
Biodegradation
19
65-75
2008
-
-
-
-
-
-
-
-
-
-
-
1
-
1
-
-
1
-
1
-
13
-
1
1
2
-
-
-
1
1
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1
-
-
-
-
-
-
1
-
-
-
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-
-
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1
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-
1
1
-
13
-
1
1
2
-
-
-
1
1
-
-
-
-
-
-
-
-
697974
Chae
Identification of genes coding ...
consortium cosmid clone pGZ1
FEMS Microbiol. Lett.
281
203-209
2008
-
-
-
-
-
-
-
-
-
-
-
-
-
3
-
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-
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-
667699
Wu
Contributions of long-range el ...
Pseudomonas sp.
Biochemistry
45
102-112
2006
-
-
-
-
1
-
-
1
-
-
-
-
-
1
-
-
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1
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2
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1
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1
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-
1
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
668613
Xu
Electrostatic influence of act ...
Pseudomonas sp.
FEBS Lett.
579
4249-4253
2005
-
-
-
-
-
-
-
-
-
-
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-
-
1
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1
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-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
670022
Dong
-
Raman evidence for product bin ...
Pseudomonas sp.
J. Raman Spectros.
36
320-325
2005
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
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1
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-
1
-
-
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-
-
-
-
-
-
-
-
-
-
-
655227
Xu
-
A QM/MM study of a nucleophili ...
Bacteria
Chem. Commun. (Camb.)
2004
892-893
2004
-
-
-
-
-
-
-
1
-
-
-
1
-
1
-
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1
-
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1
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1
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1
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-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
661288
Zhou
The purification and character ...
Arthrobacter sp., Arthrobacter sp. TM-1
Biodegradation
15
97-109
2004
-
-
-
-
-
-
-
1
-
-
2
-
-
5
-
-
1
-
-
-
1
-
2
1
1
1
-
1
1
1
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
1
-
-
2
-
-
-
-
1
-
-
1
-
2
1
1
1
-
1
1
1
-
1
-
-
-
-
-
-
669044
Xu
QM/MM studies of the enzyme-ca ...
Pseudomonas sp.
J. Am. Chem. Soc.
126
13649-13658
2004
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
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-
-
-
-
-
1
-
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-
1
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-
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-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
654718
Dong
The strength of dehalogenase-s ...
Pseudomonas sp., Pseudomonas sp. CBS-3
Biochemistry
42
9482-9490
2003
-
-
1
-
14
-
-
5
-
-
-
2
-
10
-
-
1
1
-
-
-
-
2
-
1
-
-
7
1
-
-
-
-
-
-
-
-
1
-
-
14
-
-
-
-
5
-
-
-
2
-
-
-
1
-
-
-
-
2
-
1
-
-
7
1
-
-
-
-
-
-
-
-
-
654585
Zhang
Histidine 90 function in 4-chl ...
Pseudomonas sp.
Biochemistry
40
13474-13482
2001
-
-
-
1
1
-
-
1
-
-
-
1
-
1
-
-
-
1
-
-
1
-
1
-
1
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5
1
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1
1
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-
1
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1
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-
1
-
1
-
1
-
-
5
1
-
-
-
-
-
-
-
-
-
654589
Luo
Role of active site binding in ...
Pseudomonas sp.
Biochemistry
40
15684-15692
2001
-
-
1
-
9
-
16
17
-
-
-
1
-
1
-
-
-
1
-
-
-
-
8
-
1
-
-
17
1
-
-
-
27
-
-
-
-
1
-
-
9
-
-
16
27
17
-
-
-
1
-
-
-
-
-
-
-
-
8
-
1
-
-
17
1
-
-
-
-
-
-
-
-
-
657187
Lau
The active site dynamics of 4- ...
Pseudomonas sp., Pseudomonas sp. CBS-3
Proc. Natl. Acad. Sci. USA
98
9527-9532
2001
-
-
-
-
1
-
-
-
-
-
-
2
-
10
-
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1
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2
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1
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2
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-
2
-
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-
-
-
-
-
-
-
-
-
-
33080
Taylor
Investigation of substrate act ...
Pseudomonas sp., Pseudomonas sp. CBS-3
Biochemistry
36
1349-1361
1997
-
-
-
-
7
-
-
-
-
-
-
-
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11
-
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7
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-
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-
-
-
-
-
33081
Benning
Structure of 4-chlorobenzoyl c ...
Pseudomonas sp., Pseudomonas sp. CBS-3
Biochemistry
35
8103-8109
1996
-
-
-
1
-
-
-
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-
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3
-
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1
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1
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-
33085
Yang
Identification of active site ...
Pseudomonas sp.
Biochemistry
35
10879-10885
1996
-
-
-
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3
-
2
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-
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1
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1
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3
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2
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33082
Löffler
Dehalogenation of 4-chlorobenz ...
Pseudomonas sp., Pseudomonas sp. CBS-3
Biodegradation
6
203-212
1995
-
-
-
-
-
1
9
1
-
-
2
-
-
12
-
-
1
-
-
-
1
1
8
3
1
1
3
1
1
1
5
-
-
-
-
-
-
-
-
-
-
1
-
9
-
1
-
-
2
-
-
-
-
1
-
-
1
1
8
3
1
1
3
1
1
1
5
-
-
-
-
-
-
-
33086
Crooks
-
Exploration of possible mechan ...
Arthrobacter sp., Arthrobacter sp. 4-CB1
J. Am. Chem. Soc.
117
10791-10798
1995
-
-
-
-
-
-
-
-
-
-
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-
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4
-
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1
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-
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-
-
781
Dunaway-Mariano
On the origins and functions o ...
Arthrobacter sp. 4-CB1, Arthrobacter sp., Pseudomonas sp., Pseudomonas sp. CBS-3
Biodegradation
5
259-276
1994
-
-
1
-
-
-
3
8
-
-
4
-
-
16
-
-
-
-
-
-
-
-
20
2
-
-
-
5
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
3
-
8
-
-
4
-
-
-
-
-
-
-
-
-
20
2
-
-
-
5
-
-
-
-
-
-
-
-
-
-
33077
Crooks
Purification and characterizat ...
Arthrobacter sp. 4-CB1, Arthrobacter sp.
Biochemistry
33
11645-11649
1994
-
-
-
-
-
-
-
5
-
-
-
-
-
8
-
-
1
-
-
-
1
-
10
-
-
-
-
4
1
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
5
-
-
-
-
-
-
-
1
-
-
1
-
10
-
-
-
-
4
1
-
2
-
-
-
-
-
-
-
33083
Yang
Evidence for nucleophilic cata ...
Pseudomonas sp.
Biochemistry
33
8527-8531
1994
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
33078
Liang
Specificity of 4-chlorobenzoyl ...
Pseudomonas sp., Pseudomonas sp. CBS-3
Biochemistry
32
12245-12250
1993
-
-
1
-
-
-
3
8
-
-
-
-
-
11
-
-
-
-
-
-
-
-
13
-
-
-
-
7
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
3
-
8
-
-
-
-
-
-
-
-
-
-
-
-
13
-
-
-
-
7
-
-
-
-
-
-
-
-
-
-
780
Chang
Isolation and characterization ...
Pseudomonas sp., Pseudomonas sp. CBS-3
Biochemistry
31
5605-5610
1992
-
-
1
-
-
-
-
1
-
-
3
-
-
12
-
-
1
-
-
-
1
-
2
1
-
-
-
1
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
1
-
-
3
-
-
-
-
1
-
-
1
-
2
1
-
-
-
1
-
-
-
-
-
-
-
-
-
-