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2-fluorotoluene + fumarate
(2-fluorobenzyl)succinate
-
-
-
?
3-fluorotoluene + fumarate
(3-fluorobenzyl)succinate
-
-
-
?
4-fluorotoluene + fumarate
(4-fluorobenzyl)succinate
-
-
-
?
benzaldehyde + fumarate
benzoylsuccinate
-
-
-
?
benzylsuccinate
toluene + fumarate
m-cresol + fumarate
(3-hydroxybenzyl)succinic acid
m-xylene + fumarate
(3-methylbenzyl)succinic acid
m-xylene-d6 + fumarate
(3-methylbenzyl)succinate-d6
-
-
-
?
o-cresol + fumarate
(2-hydroxybenzyl)succinic acid
o-xylene + fumarate
(2-methylbenzyl)succinic acid
o-xylene-d10 + fumarate
(2-methylbenzyl)succinate-d10
-
-
-
?
p-cresol + fumarate
(4-hydroxybenzyl)succinic acid
p-xylene + fumarate
(4-methylbenzyl)succinic acid
p-xylene-d10 + fumarate
(4-methylbenzyl)succinate-d10
-
-
-
?
toluene + fumarate
benzylsuccinate
toluene + maleate
benzylsuccinate
-
-
-
?
[d3-methyl]toluene + fumarate
?
-
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
-
-
?
[d3-methyl]toluene + maleate
?
-
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
-
-
?
benzylsuccinate

toluene + fumarate
-
-
-
?
benzylsuccinate
toluene + fumarate
-
-
-
?
benzylsuccinate
toluene + fumarate
-
-
-
?
benzylsuccinate
toluene + fumarate
-
-
-
?
benzylsuccinate
toluene + fumarate
Q39VF1;
-
-
-
?
benzylsuccinate
toluene + fumarate
Q39VF1;
-
-
-
?
benzylsuccinate
toluene + fumarate
-
-
-
?
benzylsuccinate
toluene + fumarate
-
-
-
?
benzylsuccinate
toluene + fumarate
-
-
-
?
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
-
?
benzylsuccinate
toluene + fumarate
-
-
-
?
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
-
?
m-cresol + fumarate

(3-hydroxybenzyl)succinic acid
-
-
-
-
?
m-cresol + fumarate
(3-hydroxybenzyl)succinic acid
-
-
-
-
?
m-cresol + fumarate
(3-hydroxybenzyl)succinic acid
-
-
-
-
?
m-cresol + fumarate
(3-hydroxybenzyl)succinic acid
-
-
-
-
?
m-xylene + fumarate

(3-methylbenzyl)succinic acid
-
-
-
-
?
m-xylene + fumarate
(3-methylbenzyl)succinic acid
-
-
-
-
?
m-xylene + fumarate
(3-methylbenzyl)succinic acid
-
-
-
-
?
m-xylene + fumarate
(3-methylbenzyl)succinic acid
-
-
-
-
?
o-cresol + fumarate

(2-hydroxybenzyl)succinic acid
-
-
-
-
?
o-cresol + fumarate
(2-hydroxybenzyl)succinic acid
-
-
-
-
?
o-cresol + fumarate
(2-hydroxybenzyl)succinic acid
-
-
-
-
?
o-cresol + fumarate
(2-hydroxybenzyl)succinic acid
-
-
-
-
?
o-xylene + fumarate

(2-methylbenzyl)succinic acid
-
-
-
-
?
o-xylene + fumarate
(2-methylbenzyl)succinic acid
-
-
-
-
?
o-xylene + fumarate
(2-methylbenzyl)succinic acid
-
-
-
-
?
o-xylene + fumarate
(2-methylbenzyl)succinic acid
-
-
-
-
?
p-cresol + fumarate

(4-hydroxybenzyl)succinic acid
-
-
-
-
?
p-cresol + fumarate
(4-hydroxybenzyl)succinic acid
-
-
-
-
?
p-xylene + fumarate

(4-methylbenzyl)succinic acid
-
-
-
-
?
p-xylene + fumarate
(4-methylbenzyl)succinic acid
-
-
-
-
?
toluene + fumarate

benzylsuccinate
-
-
-
?
toluene + fumarate
benzylsuccinate
-
-
-
?
toluene + fumarate
benzylsuccinate
-
-
-
?
toluene + fumarate
benzylsuccinate
-
-
-
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
-
-
?
toluene + fumarate
benzylsuccinate
-
-
-
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
-
-
-
?
toluene + fumarate
benzylsuccinate
-
-
-
-
?
toluene + fumarate
benzylsuccinate
-
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)
-
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
-
-
-
?
toluene + fumarate
benzylsuccinate
-
first step in the anaerobic degradation pathway of toluene
-
-
?
toluene + fumarate
benzylsuccinate
-
-
-
?
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
-
-
-
-
?
toluene + fumarate
benzylsuccinate
-
-
-
-
?
toluene + fumarate
benzylsuccinate
-
-
-
?
toluene + fumarate
benzylsuccinate
-
-
-
?
toluene + fumarate
benzylsuccinate
-
-
-
?
toluene + fumarate
benzylsuccinate
-
-
-
-
?
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
-
-
-
-
?
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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6500
-
alpha, alpha, beta, gamma, 1 * 97000 + 1 * 97000 + 1 * 14500 + 1 * 6500, SDS-PAGE
7000
-
gamma subunit, determined by SDS-PAGE
10000
-
alpha, alpha, beta, gamma, 1 * 94000 + 1 * 90000 + 1 * 12000 + 1 * 10000, SDS-PAGE
12000
-
alpha, alpha, beta, gamma, 1 * 94000 + 1 * 90000 + 1 * 12000 + 1 * 10000, SDS-PAGE
14000
-
beta subunit, determined by SDS-PAGE
14500
-
alpha, alpha, beta, gamma, 1 * 97000 + 1 * 97000 + 1 * 14500 + 1 * 6500, SDS-PAGE
90000
-
alpha, alpha, beta, gamma, 1 * 94000 + 1 * 90000 + 1 * 12000 + 1 * 10000, SDS-PAGE
94000
-
alpha, alpha, beta, gamma, 1 * 94000 + 1 * 90000 + 1 * 12000 + 1 * 10000, SDS-PAGE
97000
-
alpha, alpha, beta, gamma, 1 * 97000 + 1 * 97000 + 1 * 14500 + 1 * 6500, SDS-PAGE
98000
-
98000, SDS-PAGE of the alpha subunit
100000
-
alpha subunit, determined by SDS-PAGE
230000
-
determined by gel filtration, consistent with an alpha2beta2gamma2 subunit structure
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C29S
-
tutG gene, strong loss of activity, engineered strain unable to grow with toluene as carbon source
C9Y/A10S
-
tutF gene, strong loss of activity, engineered strain unable to grow with toluene as carbon source
C29S
-
tutG gene, strong loss of activity, engineered strain unable to grow with toluene as carbon source
-
C9Y/A10S
-
tutF gene, strong loss of activity, engineered strain unable to grow with toluene as carbon source
-
E509A
site-directed mutagenesis, the mutation affects binding of fumarate
F384A
site-directed mutagenesis, the mutation affects binding of toluene
L390A
site-directed mutagenesis, the mutation affects binding of toluene
L491A
site-directed mutagenesis, the mutation affects binding of toluene
Q706A
site-directed mutagenesis, the mutation affects binding of fumarate
S827A
site-directed mutagenesis, the mutation affects binding of fumarate
V708A
site-directed mutagenesis, the mutation affects binding of toluene
Y829A
site-directed mutagenesis, the mutation affects binding of toluene
F384A
-
site-directed mutagenesis, the mutation affects binding of toluene
-
L390A
-
site-directed mutagenesis, the mutation affects binding of toluene
-
L491A
-
site-directed mutagenesis, the mutation affects binding of toluene
-
V708A
-
site-directed mutagenesis, the mutation affects binding of toluene
-
Y829A
-
site-directed mutagenesis, the mutation affects binding of toluene
-
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Krieger, C.J.; Rosebooms, W.; Albrachts, P.J.; Spormann, A.M.
A stable organic free radical in anaerobic benzylsuccinate synthase of Azoarcus sp. strain T
J. Biol. Chem.
276
12924-12927
2001
Azoarcus sp., Azoarcus sp. T
brenda
Beller, H.R.; Edwards, E.A.
Anaerobic toluene activation by benzylsuccinate synthase in a highly enriched methanogenic culture
Appl. Environ. Microbiol.
66
5503-5505
2000
Desulfotomaculum, Methanospirillum sp., Methanothrix sp.
brenda
Beller, H.R.; Spormann, A.M.
Substrate range of benzylsuccinate synthase from Azoarcus sp. strain T
FEMS Microbiol. Lett.
178
147-153
1999
Azoarcus sp.
brenda
Leutwein, C.; Heider, J.
Anaerobic toluene-catabolic pathway in denitrifying Thauera aromatica: activation and beta-oxidation of the first intermediate, (R)-(+)-benzylsuccinate
Microbiology
145
3265-3271
1999
Thauera aromatica
brenda
Beller, H.R.; Spormann, A.M.
Analysis of the novel benzylsuccinate synthase reaction for anaerobic toluene activation based on structural studies of the product
J. Bacteriol.
180
5454-5457
1998
Azoarcus sp.
brenda
Leuthner, B.; Leutwein, C.; Schultz,H.; Hörth, P.; Haehnel, W.; Schiltz, E.; Schägger, H.; Heider, J.
Biochemical and genetic characterization of benzylsuccinate synthase from Thauera aromatica: a new glycyl radical enzyme catalaysing the first step in anaerobic toluene metabolism
Mol. Microbiol.
28
615-628
1998
Thauera aromatica
brenda
Verfürth, K.; Pierik, A.J.; Leutwein, C.; Zorn, S.; Heider, J.
Substrate specificities and electron paramagnetic resonance properties of benzylsuccinate synthases in anaerobic toluene and m-xylene metabolism
Arch. Microbiol.
181
155-162
2004
Azoarcus sp., Azoarcus sp. T, Thauera aromatica, Thauera aromatica K172
brenda
Qiao, C.; Marsh, E.N.G.
Mechanism of benzylsuccinate synthase: Stereochemistry of toluene addition to fumarate and maleate
J. Am. Chem. Soc.
127
8608-8609
2005
Thauera aromatica
brenda
Bhandare, R.; Calabro, M.; Coschigano, P.W.
Site-directed mutagenesis of the Thauera aromatica strain T1 tutE tutFDGH gene cluster
Biochem. Biophys. Res. Commun.
346
992-998
2006
Thauera aromatica, Thauera aromatica T1
brenda
Li, L.; Marsh, E.N.
Deuterium isotope effects in the unusual addition of toluene to fumarate catalyzed by benzylsuccinate synthase
Biochemistry
45
13932-13938
2006
Thauera aromatica
brenda
Winderl, C.; Schaefer, S.; Lueders, T.
Detection of anaerobic toluene and hydrocarbon degraders in contaminated aquifers using benzylsuccinate synthase (bssA) genes as a functional marker
Environ. Microbiol.
9
1035-1046
2007
Azoarcus sp., Azoarcus sp. T, Desulfobacula toluolica, Desulfosarcina cetonica, Desulfotomaculum sp., Desulfotomaculum sp. OX39, Geobacter grbiciae, Geobacter sp., Geobacter sp. TMJ1, Thauera aromatica, Thauera aromatica K172
brenda
Li, L.; Patterson, D.P.; Fox, C.C.; Lin, B.; Coschigano, P.W.; Marsh, E.N.
Subunit structure of benzylsuccinate synthase (dagger)
Biochemistry
48
1284-1292
2009
Thauera aromatica
brenda
Musat, F.; Galushko, A.; Jacob, J.; Widdel, F.; Kube, M.; Reinhardt, R.; Wilkes, H.; Schink, B.; Rabus, R.
Anaerobic degradation of naphthalene and 2-methylnaphthalene by strains of marine sulfate-reducing bacteria
Environ. Microbiol.
11
209-219
2009
uncultured delta proteobacterium
brenda
Vogt, C.; Cyrus, E.; Herklotz, I.; Schlosser, D.; Bahr, A.; Herrmann, S.; Richnow, H.H.; Fischer, A.
Evaluation of toluene degradation pathways by two-dimensional stable isotope fractionation
Environ. Sci. Technol.
42
7793-7800
2008
Azoarcus sp., Azoarcus sp. T, Blastochloris sulfoviridis, Desulfosarcina cetonica, Thauera aromatica
brenda
Salinero, K.; Keller, K.; Feil, W.; Feil, H.; Trong, S.; Di Bartolo, G.; Lapidus, A.
Metabolic analysis of the soil microbe Dechloromonas aromatica str. RCB: Indications of a surprisingly complex life-style and cryptic anaerobic pathways for aromatic degradation
BMC Genomics
10
351
2009
no activity in Dechloromonas aromatica RCB
brenda
Weelink, S.A.; van Doesburg, W.; Saia, F.T.; Rijpstra, W.I.; Roeling, W.F.; Smidt, H.; Stams, A.J.
A strictly anaerobic betaproteobacterium Georgfuchsia toluolica gen. nov., sp. nov. degrades aromatic compounds with Fe(III), Mn(IV) or nitrate as an electron acceptor
FEMS Microbiol. Ecol.
70
575-585
2009
Georgfuchsia toluolica, Georgfuchsia toluolica G5G6
brenda
Winderl, C.; Penning, H.; Netzer, F.V.; Meckenstock, R.U.; Lueders, T.
DNA-SIP identifies sulfate-reducing Clostridia as important toluene degraders in tar-oil-contaminated aquifer sediment
ISME J.
4
1314-1325
2010
Clostridia
brenda
Hilberg, M.; Pierik, A.J.; Bill, E.; Friedrich, T.; Lippert, M.L.; Heider, J.
Identification of FeS clusters in the glycyl-radical enzyme benzylsuccinate synthase via EPR and Moessbauer spectroscopy
J. Biol. Inorg. Chem.
17
49-56
2012
Escherichia coli
brenda
Bharadwaj, V.S.; Dean, A.M.; Maupin, C.M.
Insights into the glycyl radical enzyme active site of benzylsuccinate synthase: a computational study
J. Am. Chem. Soc.
135
12279-12288
2013
Thauera sp. (Q8L1A3), Thauera sp. DNT-1 (Q8L1A3)
brenda
Kuemmel, S.; Kuntze, K.; Vogt, C.; Boll, M.; Heider, J.; Richnow, H.H.
Evidence for benzylsuccinate synthase subtypes obtained by using stable isotope tools
J. Bacteriol.
195
4660-4667
2013
Azoarcus sp. (Q8VPT7), Azoarcus sp. T (Q8VPT7), Desulfosarcina cetonica (A2TBP7), Desulfosarcina cetonica DSM 7267 (A2TBP7), Geobacter metallireducens (Q39VF1), Geobacter metallireducens GS-15 / ATCC 53774 / DSM 7210 (Q39VF1), Thauera aromatica (O87943), Thauera aromatica K172 (O87943)
brenda