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Information on EC 1.14.12.13 - 2-halobenzoate 1,2-dioxygenase
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1.14.12.13 2-halobenzoate 1,2-dioxygenaseIUBMB Comments
A multicomponent enzyme system composed of a dioxygenase component and an electron transfer component. The latter contains FAD. The enzyme, characterized from the bacterium Burkholderia cepacia 2CBS, has a broad substrate specificity. Substrates include 2-fluorobenzoate, 2-chlorobenzoate, 2-bromobenzoate, and 2-iodobenzoate, which are processed in this order of preference.
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Word Map
- 1.14.12.13
- cepacia
- catechol
- chlorobenzoates
- burkholderia
- toluate
- chlorocatechols
- biphenyls
-
rieske-type
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cupriavidus
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ortho-cleavage
- cydab
-
regiospecificity
- necator
-
polychlorinated
- quinol
- 4-chlorocatechol
- benabc
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tn5-based
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monochlorobiphenyls
- 2,4-dichlorobenzoate
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aroclor
- cis,cis-muconate
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co-oxidize
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minitransposon
The enzyme appears in viruses and cellular organisms
Synonyms
2-halobenzoate 1,2-dioxygenase, cbdabc, 2-halobenzoate dioxygenase, 2-chlorobenzoate 1,2-dioxygenase, cbdab, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(chloro)benzoate dioxygenase
2-chlorobenzoate 1,2-dioxygenase
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-
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2-halobenzoate 1,2-dioxygenase
2-halobenzoate dioxygenase
BenA
cbdABC
2-halobenzoate 1,2-dioxygenase
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-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2-chlorobenzoate + NADH + H+ + O2 = catechol + chloride + NAD+ + CO2
broad substrate specificity, ability to transform all 3 monochlorobenzoates almost equally well. Enzyme appears to lack absolute regioselectivity
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2-chlorobenzoate + NADH + H+ + O2 = catechol + chloride + NAD+ + CO2
two-component nonheme iron dioxygenase system of oxygenase system class IB dioxygenase: NADH:acceptor reductase containing both FAD and cloroplast-type 2Fe-2S and Rieske-type 2Fe-2S-containing oxygenase component
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2-chlorobenzoate + NADH + H+ + O2 = catechol + chloride + NAD+ + CO2
inducible two-component enzyme system: component B is an iron-sulfur flavoprotein (reductase) and red-brown component A (oxygenase) is an iron-sulfur protein
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2-chlorobenzoate + NADH + H+ + O2 = catechol + chloride + NAD+ + CO2
multi-component dioxygenase system proposed: 1,2-hydroxylating, dehalogenating, decarboxylating
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2-chlorobenzoate + NADH + H+ + O2 = catechol + chloride + NAD+ + CO2
EPR, electron spin echo envelope modulation, electron nuclear double resonance studies and the electrochemical potential are performed. Enzyme contains one ferredoxin-type (reductase) and one Rieske-type (oxygenase) 2Fe2S center
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2-chlorobenzoate + NADH + H+ + O2 = catechol + chloride + NAD+ + CO2
broad substrate specificity, ability to transform all 3 monochlorobenzoates almost equally well. Enzyme appears to lack absolute regioselectivity
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2-chlorobenzoate + NADH + H+ + O2 = catechol + chloride + NAD+ + CO2
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
decarboxylation
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dehalogenation
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hydroxylation
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-
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oxidation
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redox reaction
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reduction
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-
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PATHWAY SOURCE
PATHWAYS
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-
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SYSTEMATIC NAME
IUBMB Comments
2-halobenzoate,NADH:oxygen oxidoreductase (1,2-hydroxylating, dehalogenating, decarboxylating)
A multicomponent enzyme system composed of a dioxygenase component and an electron transfer component. The latter contains FAD. The enzyme, characterized from the bacterium Burkholderia cepacia 2CBS, has a broad substrate specificity. Substrates include 2-fluorobenzoate, 2-chlorobenzoate, 2-bromobenzoate, and 2-iodobenzoate, which are processed in this order of preference.
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CAS REGISTRY NUMBER
COMMENTARY
125268-83-9
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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
2,6-dichlorobenzoate + NADH + O2
? + NAD+ + CO2
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19% of the activity with 2-chlorobenzoate
-
-
?
2-amino-4-chlorobenzoate + NADH + O2
? + NAD+ + CO2
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28% of the activity with 2-chlorobenzoate
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-
?
2-amino-5-chlorobenzoate + NADH + O2
? + NAD+ + CO2
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27% of the activity with 2-chlorobenzoate
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-
?
2-chloro-5-bromobenzoate + NADH + O2
4-bromocatechol + chloride + NAD+ + CO2
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50% of the activity with 2-chlorobenzoate
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-
?
3,4-dichlorobenzoate + NADH + O2
? + NAD+ + CO2
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10% of the activity with 2-chlorobenzoate
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-
?
3,5-dichlorobenzoate + NADH + O2
? + NAD+ + CO2
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16% of the activity with 2-chlorobenzoate
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-
?
3-chlorobenzoate + NADH + H+ + O2
3-chlorocatechol + NAD+ + CO2
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-
-
?
3-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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15% of the activity with 2-chlorobenzoate
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-
?
4-amino-2-chlorobenzoate + NADH + O2
4-aminocatechol + chloride + NAD+ + CO2
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21% of the activity with 2-chlorobenzoate
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-
?
4-chlorobenzoate + NADH + H+ + O2
4-chlorocatechol + NAD+ + CO2
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-
-
?
4-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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21% of the activity with 2-chlorobenzoate
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-
?
benzoate + NADH + H+ + O2
3,5-cyclohexadiene-1,2-diol + NAD+ + CO2
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37% of the activity with 2-chlorobenzoate
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-
?
2,4-dichlorobenzoate + NADH + O2
4-chlorocatechol + chloride + NAD+ + CO2
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50% of the activity with 2-chlorobenzoate
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-
?
2,4-dichlorobenzoate + NADH + O2
4-chlorocatechol + chloride + NAD+ + CO2
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50% of the activity with 2-chlorobenzoate
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-
?
2,5-dichlorobenzoate + NADH + O2
4-chlorocatechol + chloride + NAD+ + CO2
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38% of the activity with 2-chlorobenzoate
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-
?
2,5-dichlorobenzoate + NADH + O2
4-chlorocatechol + chloride + NAD+ + CO2
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38% of the activity with 2-chlorobenzoate
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-
?
2,5-dichlorobenzoate + NADH + O2
4-chlorocatechol + chloride + NAD+ + CO2
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-
-
?
2,5-dichlorobenzoate + NADH + O2
4-chlorocatechol + chloride + NAD+ + CO2
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-
-
?
2,5-dichlorobenzoate + NADH + O2
4-chlorocatechol + NAD+ + Cl- + CO2
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involved in the metabolism of 2,5-dichlorobenzoate
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?
2,5-dichlorobenzoate + NADH + O2
4-chlorocatechol + NAD+ + Cl- + CO2
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involved in the metabolism of 2,5-dichlorobenzoate
-
?
2-bromobenzoate + NADH + O2
catechol + bromide + NAD+ + CO2
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-
-
?
2-bromobenzoate + NADH + O2
catechol + bromide + NAD+ + CO2
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-
-
?
2-bromobenzoate + NADH + O2
catechol + bromide + NAD+ + CO2
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107% of the activity with 2-chlorobenzoate
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-
?
2-bromobenzoate + NADH + O2
catechol + bromide + NAD+ + CO2
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107% of the activity with 2-chlorobenzoate
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-
?
2-chlorobenzoate + NADH + H+ + O2
3-chlorocatechol + NAD+ + CO2
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-
-
?
2-chlorobenzoate + NADH + H+ + O2
3-chlorocatechol + NAD+ + CO2
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-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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the oxygen in the enzymatically catechol is derived from molecular oxygen, the formed byproduct 2,3-dihydroxybenzoate is suggested to be a dead end metabolite
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?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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initial step in the degradation of aromatic compounds
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?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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first step of 2-chlorobenzoate degradation via meta-cleavage
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?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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first step of 2-chlorobenzoate degradation via meta-cleavage
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?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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no growth on 2-chlorobenzoate
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?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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no growth on 2-chlorobenzoate
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?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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-
-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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-
-
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?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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involved in the metabolism of 2-chlorobenzoate
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?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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-
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?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
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involved in the metabolism of 2-chlorobenzoate
-
?
2-fluorobenzoate + NADH + O2
catechol + fluoride + NAD+ + CO2
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-
-
?
2-fluorobenzoate + NADH + O2
catechol + fluoride + NAD+ + CO2
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-
-
?
2-iodobenzoate + NADH + O2
catechol + iodide + NAD+ + CO2
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-
-
?
2-iodobenzoate + NADH + O2
catechol + iodide + NAD+ + CO2
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-
-
?
2-iodobenzoate + NADH + O2
catechol + iodide + NAD+ + CO2
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130% of the activity with 2-chlorobenzoate
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?
2-iodobenzoate + NADH + O2
catechol + iodide + NAD+ + CO2
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130% of the activity with 2-chlorobenzoate
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?
2-methylbenzoate + NADH + O2
o-cresol + ? + NAD+ + CO2
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named o-toluate
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?
3-chlorobenzoate + NADH + H+ + O2
4-chlorocatechol + NAD+ + CO2
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-
-
?
3-chlorobenzoate + NADH + H+ + O2
4-chlorocatechol + NAD+ + CO2
-
-
-
?
benzoate + NADH + H+ + O2
catechol + NAD+ + CO2
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2-chloro-3,5-cyclohexadiene-1,2-diol-1-carboxylic acid as unstable intermediate
-
?
benzoate + NADH + H+ + O2
catechol + NAD+ + CO2
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2-chloro-3,5-cyclohexadiene-1,2-diol-1-carboxylic acid as unstable intermediate
-
?
additional information
?
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very broad substrate specificity is listed, benzoate analogs with substituents in ortho position are preferred. Trichloroethylene, dihydroxybenzoates, benzene chlorobenzene, toluene, phenol and chlorophenylacetate isomers do not serve as substrates
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
2,5-dichlorobenzoate + NADH + O2
4-chlorocatechol + NAD+ + Cl- + CO2
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involved in the metabolism of 2,5-dichlorobenzoate
-
?
2,5-dichlorobenzoate + NADH + O2
4-chlorocatechol + NAD+ + Cl- + CO2
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involved in the metabolism of 2,5-dichlorobenzoate
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
-
-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
-
initial step in the degradation of aromatic compounds
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
-
first step of 2-chlorobenzoate degradation via meta-cleavage
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
-
first step of 2-chlorobenzoate degradation via meta-cleavage
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
-
-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
-
-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
-
-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
-
involved in the metabolism of 2-chlorobenzoate
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
-
-
-
-
?
2-chlorobenzoate + NADH + H+ + O2
catechol + chloride + NAD+ + CO2
-
involved in the metabolism of 2-chlorobenzoate
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FAD
-
component B contains 0.8 mol per mol of enzyme, 0.002 mM increases activity
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Fe2+
Sulfide
Fe2+
-
iron atoms are coordinated by 4 cysteines and are bridged by a pair of acid-labile sulfur atoms in the 2Fe2S ferredoxins
Fe2+
-
component B contains 1.7 mol and A 5.8 mol of iron per mol of enzyme
Fe2+
-
required, ability to retain the endogenous Fe2+ during the crude extract perparation
Sulfide
-
iron atoms are coordinated by 4 cysteines and are bridged by a pair of acid-labile sulfur atoms in the 2Fe2S ferredoxins
Sulfide
-
component B contains 1.7 mol and A 6.0 mol of acid-labile sulfide per mol of enzyme
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.063 - 0.079
2,5-dichlorobenzoate
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cells grown on 2-chlorobenzoate or 2,5-dichlorobenzoate
0.078 - 0.117
2-Chlorobenzoate
-
cells grown on 2-chlorobenzoate or 2,5-dichlorobenzoate
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.0013
-
cells are grown on 3-chlorobenzoate, benzoate as substrate for assay
0.0024
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recombinant cells are grown on LB/IPTG, benzoate as substrate for assay
0.018 - 0.023
-
cells grown on 2-clorobenzoate or 2,5-dichlorobenzoate, enzyme activity for the conversion of both substrates
0.53
-
activity of component A after gel filtration in presence of component B
additional information
-
activity is similarly influenced by pH, temperature, concentration of oxygen, protein, Fe2+, FAD and NADH in assay medium independent if the cells are grown on 2-chlorobenzoate or 2,5-dichlorobenzoate
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
30
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
is involved in the initial attack of chlorobenzoates
physiological function
is involved in the initial attack of chlorobenzoates
Show AA Sequence and Transmembrane Helices (643 entries)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
19500
-
x * 19500, x * 52400, alpha3beta3, small and large subunit of the oxygenase component, SDS-PAGE
20000
-
3 * 52000, 3 * 20000, alpha3,beta3 structure of component A, SDS-PAGE
52000
-
3 * 52000, 3 * 20000, alpha3,beta3 structure of component A, SDS-PAGE
52400
-
x * 19500, x * 52400, alpha3beta3, small and large subunit of the oxygenase component, SDS-PAGE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hexamer
-
3 * 52000, 3 * 20000, alpha3,beta3 structure of component A, SDS-PAGE
monomer
oligomer
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x * 19500, x * 52400, alpha3beta3, small and large subunit of the oxygenase component, SDS-PAGE
additional information
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
mutants are made by treatment with N-methyl-N'-nitro-N-nitrosoguanidine, mutants are unable to grow on 2-chlorobenzoate and catechol
additional information
-
several mutants of Pseudomonas cepacia, putida and sp. are used