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Enzyme Nomenclature
Information on EC 4.1.99.11 - benzylsuccinate synthase
for references in articles please use BRENDA:EC4.1.99.11
Word Map on EC 4.1.99.11
- 4.1.99.11
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denitrifying
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glycyl
- thauera
- aromatica
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sulfate-reducing
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toluene-degrading
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aquifer
- ethylbenzene
- azoarcus
- benzoyl-coa
- geobacter
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hydrocarbon-degrading
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r-benzylsuccinate
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plume
- 2-methylnaphthalene
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hydrocarbon-contaminated
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iron-reducing
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formate-lyase
- m-xylene
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nitrate-reducing
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toluene-grown
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feiii-reducing
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compound-specific
- desulfobulbaceae
- environmental protection
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toluene-induced
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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
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EC NUMBER 
COMMENTARY 
4.1.99.11
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RECOMMENDED NAME
GeneOntology No.
benzylsuccinate synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
benzylsuccinate = toluene + fumarate
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benzylsuccinate = toluene + fumarate
stereospecific radical addition of toluene to fumarate, enzyme carries a stable organic free radical, most probably located on glycine residue 828
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benzylsuccinate = toluene + fumarate
substrate binding stabilizing the active site and reaction mechanism via glycyl radical, detailed overview. Syn addition of toluene to fumaric acid and facilitation of a mechanism that retains the hydrogen abstracted from the methyl group of toluene within the succinyl moiety. The stability of substrates at the active site and the occurrence of feasible radical transfer distances between the thiyl radical, substrates, and the active site glycine indicate a substrate-assisted radical transfer pathway governing fumarate addition
benzylsuccinate = toluene + fumarate
stereospecific radical addition of toluene to fumarate, enzyme carries a stable organic free radical, most probably located on glycine residue 828
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benzylsuccinate = toluene + fumarate
substrate binding stabilizing the active site and reaction mechanism via glycyl radical, detailed overview. Syn addition of toluene to fumaric acid and facilitation of a mechanism that retains the hydrogen abstracted from the methyl group of toluene within the succinyl moiety. The stability of substrates at the active site and the occurrence of feasible radical transfer distances between the thiyl radical, substrates, and the active site glycine indicate a substrate-assisted radical transfer pathway governing fumarate addition
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
addition
addition
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
benzylsuccinate fumarate-lyase (toluene-forming)
A glycyl radical enzyme that is inhibited by benzyl alcohol, benzaldehyde, phenylhydrazine and is inactivated by oxygen.
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CAS REGISTRY NUMBER
COMMENTARY
209264-18-6
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
metabolism
physiological function
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a novel benzylsuccinate synthase alpha-subunit (bssA) sequence type in sedimentary microbial community originating from a tar-oil-contaminated aquifer at a former coal gasification plant
additional information
metabolism
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BSSA gene encoding the alpha-subunit of Bss from a novel taxon of the Betaproteobacteria catalyzes the first step in anaerobic toluene degradation
metabolism
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BSSA gene encoding the alpha-subunit of Bss from a novel taxon of the Betaproteobacteria catalyzes the first step in anaerobic toluene degradation
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additional information
the catalytic subunit has the putative radical sites located on Cys492 and Gly828, induced-fit product docking approach and substrate-bound molecular dynamics simulations based on the refined active site topology, three-dimensional structure homology modeling, overview
additional information
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the catalytic subunit has the putative radical sites located on Cys492 and Gly828, induced-fit product docking approach and substrate-bound molecular dynamics simulations based on the refined active site topology, three-dimensional structure homology modeling, overview
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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
[d3-methyl]toluene + fumarate
?
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deuterium is transferred from toluene to the C-3 pro-(S) position of benzylsuccinate, implying that the addition of toluene to the double bond of fumarate is syn
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-
?
[d3-methyl]toluene + maleate
?
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addition of toluene occurs in anti fashion. Formation of the C-3 radical of the benzylsuccinate as an intermediate, in which rotation about the C-2-C-3 bond can occur to relieve the sterically unfavorable cis conformation
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-
?
benzylsuccinate
toluene + fumarate
enzyme-substrate interactions at the active site by molecular dynamics simulations, overview
involvement of Phe384, Leu390, Leu491, Tyr829, and Val708 in stabilizing toluene binding and Ser827, Glu509, and Gln706 in stabilizing fumaric acid binding
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?
benzylsuccinate
toluene + fumarate
enzyme-substrate interactions at the active site by molecular dynamics simulations, overview
involvement of Phe384, Leu390, Leu491, Tyr829, and Val708 in stabilizing toluene binding and Ser827, Glu509, and Gln706 in stabilizing fumaric acid binding
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?
toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
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-
?
toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
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-
?
toluene + fumarate
benzylsuccinate
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on incubation of fresh sediments with (13)C(7)-toluene, the production of both sulfide and (13)CO(2) is coupled to the (13)C-labeling of DNA of microbes related to Desulfosporosinus spp. within the Peptococcaceae (Clostridia)
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-
?
toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
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-
?
toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
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-
?
toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
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-
?
toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
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-
?
toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
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-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
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-
?
toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
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-
?
toluene + fumarate
benzylsuccinate
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highly stereospecific, enantiomer purity for (R-)-(+)-benzylsuccinate 99%
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?
toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
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-
?
toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
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-
ir
toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
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-
?
toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
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-
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
benzylsuccinate
toluene + fumarate
Geobacter metallireducens GS-15 / ATCC 53774 / DSM 7210
Q39VF1
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-
-
?
toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
highly stereospecific, enantiomer purity for (R-)-(+)-benzylsuccinate 99%
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
ir
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
[4Fe-4S] center
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[4 Fe-4S] clusters in benzylsuccinate synthase are identified via EPR and Mossbauer spectroscopy
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
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tutE gene product (benzylsuccinate synthase activating enzyme) required for activity, changes in the tutE encoded protein (C72A and C79A) are able to prevent the action of benzylsuccinate synthase; tutH gene product required for activity, changes in the tutH encoded protein (G52A/K53R/S54A) are able to prevent the action of benzylsuccinate synthase, tutH gene product possibly involved in assembly of the enzyme subunits
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.016
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
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PDB
SCOP
CATH
ORGANISM
UNIPROT
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6500
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alpha, alpha, beta, gamma, 1 * 97000 + 1 * 97000 + 1 * 14500 + 1 * 6500, SDS-PAGE
10000
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alpha, alpha, beta, gamma, 1 * 94000 + 1 * 90000 + 1 * 12000 + 1 * 10000, SDS-PAGE
12000
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alpha, alpha, beta, gamma, 1 * 94000 + 1 * 90000 + 1 * 12000 + 1 * 10000, SDS-PAGE
14500
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alpha, alpha, beta, gamma, 1 * 97000 + 1 * 97000 + 1 * 14500 + 1 * 6500, SDS-PAGE
90000
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alpha, alpha, beta, gamma, 1 * 94000 + 1 * 90000 + 1 * 12000 + 1 * 10000, SDS-PAGE
94000
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alpha, alpha, beta, gamma, 1 * 94000 + 1 * 90000 + 1 * 12000 + 1 * 10000, SDS-PAGE
97000
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alpha, alpha, beta, gamma, 1 * 97000 + 1 * 97000 + 1 * 14500 + 1 * 6500, SDS-PAGE
230000
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determined by gel filtration, consistent with an alpha2beta2gamma2 subunit structure
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hexamer
tetramer
hexamer
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alpha2 beta2 gamma2, three subunits encoded by the genes tutF, tutD, and tutG
hexamer
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the structural model for benzylsuccinate synthase proposes an alpha2beta2gamma2-complex
hexamer
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alpha2 beta2 gamma2, three subunits encoded by the genes tutF, tutD, and tutG
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tetramer
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alpha, alpha', beta, gamma, 1 * 97000 + 1 * 97000 + 1 * 14500 + 1 * 6500, SDS-PAGE
tetramer
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alpha, alpha', beta, gamma, 1 * 94000 + 1 * 90000 + 1 * 12000 + 1 * 10000, SDS-PAGE
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OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
extremely oxygen sensitive
rapidly inactivated by oxygen with a half-life of 20-30 s upon exposure to air
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210663
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DEAE-Sepharose, hydroxyapatite, anion exchange chromatography, enzyme severely inactivated during purification
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hydroxyapatite, gel filtration, 95% loss of specific activity after gel filtration
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli BL21DE3 cells, the vectors pET-28b, pACYC-Duet, pET-Duet and pRSF-Duet are used
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gene bssA, phylogenetic analysis
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C29S
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tutG gene, strong loss of activity, engineered strain unable to grow with toluene as carbon source
C9Y/A10S
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tutF gene, strong loss of activity, engineered strain unable to grow with toluene as carbon source
C29S
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tutG gene, strong loss of activity, engineered strain unable to grow with toluene as carbon source
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C9Y/A10S
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tutF gene, strong loss of activity, engineered strain unable to grow with toluene as carbon source
-
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Renatured/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
environmental protection
additional information
environmental protection
-
toluene is a widespread contaminant and can be degraded under anoxic conditions, catalyzed by benzylsuccinate synthase
environmental protection
-
toluene is a widespread contaminant and can be degraded under anoxic conditions, catalyzed by benzylsuccinate synthase
environmental protection
-
toluene is a widespread contaminant and can be degraded under anoxic conditions, catalyzed by benzylsuccinate synthase
environmental protection
-
toluene is a widespread contaminant and can be degraded under anoxic conditions, catalyzed by benzylsuccinate synthase
environmental protection
-
toluene is a widespread contaminant and can be degraded under anoxic conditions, catalyzed by benzylsuccinate synthase
-
additional information
-
target for the detection of toluene degrading organisms in environmental samples
additional information
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target for the detection of toluene degrading organisms in environmental samples
additional information
-
target for the detection of toluene degrading organisms in environmental samples
additional information
-
target for the detection of toluene degrading organisms in environmental samples
additional information
-
target for the detection of toluene degrading organisms in environmental samples
additional information
-
target for the detection of toluene degrading organisms in environmental samples
additional information
-
target for the detection of toluene degrading organisms in environmental samples
additional information
-
target for the detection of toluene degrading organisms in environmental samples
-
additional information
-
target for the detection of toluene degrading organisms in environmental samples
-
additional information
-
target for the detection of toluene degrading organisms in environmental samples
-
additional information
-
target for the detection of toluene degrading organisms in environmental samples
-
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