Information on EC 1.14.12.10 - benzoate 1,2-dioxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.12.10
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RECOMMENDED NAME
GeneOntology No.
benzoate 1,2-dioxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
benzoate + NADH + H+ + O2 = (1R,6S)-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylate + NAD+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
reduction
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
benzoate degradation I (aerobic)
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Benzoate degradation
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Fluorobenzoate degradation
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Metabolic pathways
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Microbial metabolism in diverse environments
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SYSTEMATIC NAME
IUBMB Comments
benzoate,NADH:oxygen oxidoreductase (1,2-hydroxylating)
A system, containing a reductase which is an iron-sulfur flavoprotein (FAD), and an iron-sulfur oxygenase. Requires Fe2+.
CAS REGISTRY NUMBER
COMMENTARY hide
9059-18-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain BADO ADP1
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Manually annotated by BRENDA team
strain PHEA-2
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Manually annotated by BRENDA team
strain ADP1, class IB dioxygenase
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Manually annotated by BRENDA team
strain HS-2
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Manually annotated by BRENDA team
strain HS-2
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Manually annotated by BRENDA team
strain KT 2440
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Manually annotated by BRENDA team
strain KT2240 and KTSY01
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Manually annotated by BRENDA team
strain 19070
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Manually annotated by BRENDA team
strain 19070
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-methylbenzoate + O2 + NADH
cis-1,2-dihydro-1,2-dihydroxy-2-methyl-benzoate + NAD+
show the reaction diagram
3-aminobenzoate + O2 + NADH
3-amino-2-hydro-1,2-dihydroxybenzoate
show the reaction diagram
3-chlorobenzoate + O2 + NADH
3-chloro-2-hydro-1,2-dihydroxybenzoate
show the reaction diagram
3-chlorobenzoate + O2 + NADH
3-chloro-2-hydro-1,2-dihydroxybenzoate + NAD+
show the reaction diagram
3-fluorobenzoate + O2 + NADH
3-fluoro-2-hydro-1,2-dihydroxybenzoate
show the reaction diagram
3-fluorobenzoate + O2 + NADH
3-fluoro-2-hydro-1,2-dihydroxybenzoate + NAD+
show the reaction diagram
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-
-
-
?
3-methylbenzoate + O2 + NADH
3-methyl-2-hydro-1,2-dihydroxybenzoate
show the reaction diagram
3-methylbenzoate + O2 + NADH
3-methyl-2-hydro-1,2-dihydroxybenzoate + NAD+
show the reaction diagram
4-fluorobenzoate + O2 + NADH
4-fluoro-2-hydro-1,2-dihydroxybenzoate
show the reaction diagram
benzene + O2 + NADH
(R,S)-1,2-dihydro-1,2-dihydroxycatechol + NAD+
show the reaction diagram
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benzoate + NADH + H+ + O2
(1R,6S)-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylate + NAD+
show the reaction diagram
benzoate + NADH + H+ + O2
cis-1,2-dihydroxy-cyclohexa-3,5-diene-1-carboxylate + NAD+
show the reaction diagram
benzoate + O2 + NADH
2-hydro-1,2-dihydroxybenzoate + NAD+
show the reaction diagram
benzoate + O2 + NADH + H+
2-hydro-1,2-dihydroxybenzoate + NAD+
show the reaction diagram
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
benzoate + NADH + H+ + O2
(1R,6S)-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylate + NAD+
show the reaction diagram
benzoate + NADH + H+ + O2
cis-1,2-dihydroxy-cyclohexa-3,5-diene-1-carboxylate + NAD+
show the reaction diagram
benzoate + O2 + NADH
2-hydro-1,2-dihydroxybenzoate + NAD+
show the reaction diagram
benzoate + O2 + NADH + H+
2-hydro-1,2-dihydroxybenzoate + NAD+
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
iron-sulfur center
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each alpha-subunit contains a Rieske [2Fe-2S] cluster and a mononuclear iron site
iron-sulfur centre
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[2Fe-2S] Rieske center
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.401
2-Methylbenzoate
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pH 7, 25C
0.113
3-chlorobenzoate
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pH 7, 25C
0.089
3-methylbenzoate
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pH 7, 25C
0.0039 - 0.026
Benzoate
0.0048
NADH
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0.026
NADH-cytochrome c reductase component
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0.0043
O2
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4.2
2-Methylbenzoate
Acinetobacter calcoaceticus
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pH 7, 25C
3
3-chlorobenzoate
Acinetobacter calcoaceticus
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pH 7, 25C
7
3-methylbenzoate
Acinetobacter calcoaceticus
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pH 7, 25C
8.6 - 367
Benzoate
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
1.36
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benzoate oxygenase
5
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pH 7, 25C, with 3-methylbenzoate as substrate
790
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benzoate reductase, reduction of K3Fe(CN)6
additional information
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The recombinant bacteria shows a BZDO activity of 1.2 mmol benzoate per gram cell dry weight, while Pseudomonas putida KTSY01 shows a BZDO activity of only 0.09 mmol.
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.7
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oxygenase component
7
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assay at
8.2
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NADH-cytochrome c reductase component
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 8
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pH 6.0: about 55% activity, pH 8.0: about 60% activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
24
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assay at
30
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assay at
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.54
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alpha-subunit BenA, calculated from amino acid sequence
PDB
SCOP
CATH
ORGANISM
UNIPROT
Burkholderia mallei (strain ATCC 23344)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37500
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NADH-cytochrome c component
38000
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reductase component
51500
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alpha-subunit BenA, calculated from amino acid sequence
52300
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calculated from the deduced amino acid sequence, alpha subunit
195000
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oxygenase component, sedimentation analysis; sedimentation analysis
201000
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sedimentation equilibrium
204000
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SDS-PAGE
270000
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oxygenase component, gel filtration
273000
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oxygenase component, sedimentation equilibrium
280000
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oxygenase component, native PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hexamer
monomer
trimer
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
Pseudomonas putida may be one of these bacteria that exhibits a strong tolerance to the toxicity of benzoate.
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80C, stable for at least 6 months
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
benzoate oxgenase and reductase component; DEAE-Sepharose Fast Flow column chromatography and Ultrogel AcA 34 gel filtration
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oxygenase component
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Q-Sepharose column chromatography and Superdex 200 GPC column gel filtration
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recombinant and native enzyme
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Pseudomonas putida CL01 as His-tag fusion protein
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expression of presumed dioxygenase component in Escherichia coli
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The genes benABC encoding benzoate dioxygenase are cloned into plasmid pSYM01 which harboring a cis-diol dehydrogenase knockout and overexpressed in Pseudomona putida KTSY01.
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when expressed in Escherichia coli, benzoate 1,2-dioxygenase transforms benzoate into cis-benzoate dihydrodiol
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
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