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benzylsuccinate = toluene + fumarate
benzylsuccinate = toluene + fumarate
mechanism
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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
benzylsuccinate synthase (BSS) catalyzes the formation of a C-C bond between toluene and fumarate by a radical mechanism, overview. An enzyme-bound glycyl radical cofactor transiently forms a catalytically essential enzyme-bound thiyl (Cys) radical
benzylsuccinate = toluene + fumarate
benzylsuccinate synthase (BSS) catalyzes the formation of a C-C bond between toluene and fumarate by a radical mechanism. BSS binds substrates in a buried active site and uses conformational changes to gate access. The C-C bond-forming reaction performed by BSS requires an oxygen-sensitive radical cofactor. BSS contains a backbone glycyl radical in its activated form. The two substrates adopt orientations that appear ideal for radical-mediated C-C bond formation, the methyl group of toluene is positioned between fumarate and a cysteine that forms a thiyl radical during catalysis, which is in turn adjacent to the glycine that serves as a radical storage residue. Toluene is held in place by fumarate on one face and tight packing by hydrophobic residues on the other face and sides. These hydrophobic residues appear to become ordered, thus encapsulating toluene, only in the presence of BSSbeta, a small protein subunit that forms a tight complex with BSSalpha, the catalytic subunit. Substrates can enter the active site through a channel, which can be blocked by subunit beta, BSSbeta plays a role in gating active site accessibility
benzylsuccinate = toluene + fumarate
DFT model of the reaction mechanism of BSS, mechanistic modeling
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benzylsuccinate = toluene + fumarate
DFT model of the reaction mechanism of BSS, mechanistic modeling
benzylsuccinate = toluene + fumarate
DFT model of the reaction mechanism of BSS, mechanistic modeling
benzylsuccinate = toluene + fumarate
reaction mechanism of enzymatic radical C-C coupling by benzylsuccinate synthase, molecular dynamics (MD) simulations and quantum mechanics (QM) modeling, detailed overview. The enzyme is a glycyl radical enzyme that catalyzes the enantiospecific fumarate addition to toluene initiating its anaerobic metabolism in the denitrifying bacterium Thauera aromatica, and this reaction represents the general mechanism of toluene degradation in all known anaerobic degraders. The enantiospecificity of the enzyme seems to be enforced by a thermodynamic preference for binding of fumarate in the pro-(R)-orientation and reverse preference of benzyl radical attack on fumarate in pro-(S)-pathway which results with prohibitively high energy barrier of the radical quenching
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
DFT model of the reaction mechanism of BSS, mechanistic modeling
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benzylsuccinate = toluene + fumarate
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2-fluorotoluene + fumarate
(2-fluorobenzyl)succinate
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3-fluorotoluene + fumarate
(3-fluorobenzyl)succinate
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4-fluorotoluene + fumarate
(4-fluorobenzyl)succinate
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benzaldehyde + fumarate
benzoylsuccinate
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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
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o-cresol + fumarate
(2-hydroxybenzyl)succinic acid
o-xylene + fumarate
(2-methylbenzyl)succinic acid
o-xylene-d10 + fumarate
(2-methylbenzyl)succinate-d10
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?
p-cresol + fumarate
(4-hydroxybenzyl)succinic acid
p-xylene + fumarate
(4-methylbenzyl)succinic acid
p-xylene-d10 + fumarate
(4-methylbenzyl)succinate-d10
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?
toluene + fumarate
benzylsuccinate
toluene + maleate
benzylsuccinate
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[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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additional information
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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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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m-cresol + fumarate
(3-hydroxybenzyl)succinic acid
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m-cresol + fumarate
(3-hydroxybenzyl)succinic acid
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m-cresol + fumarate
(3-hydroxybenzyl)succinic acid
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m-cresol + fumarate
(3-hydroxybenzyl)succinic acid
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m-xylene + fumarate
(3-methylbenzyl)succinic acid
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m-xylene + fumarate
(3-methylbenzyl)succinic acid
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m-xylene + fumarate
(3-methylbenzyl)succinic acid
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m-xylene + fumarate
(3-methylbenzyl)succinic acid
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o-cresol + fumarate
(2-hydroxybenzyl)succinic acid
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o-cresol + fumarate
(2-hydroxybenzyl)succinic acid
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o-cresol + fumarate
(2-hydroxybenzyl)succinic acid
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o-cresol + fumarate
(2-hydroxybenzyl)succinic acid
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o-xylene + fumarate
(2-methylbenzyl)succinic acid
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o-xylene + fumarate
(2-methylbenzyl)succinic acid
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o-xylene + fumarate
(2-methylbenzyl)succinic acid
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o-xylene + fumarate
(2-methylbenzyl)succinic acid
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p-cresol + fumarate
(4-hydroxybenzyl)succinic acid
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p-cresol + fumarate
(4-hydroxybenzyl)succinic acid
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p-xylene + fumarate
(4-methylbenzyl)succinic acid
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p-xylene + fumarate
(4-methylbenzyl)succinic acid
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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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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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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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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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toluene + fumarate
benzylsuccinate
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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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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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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
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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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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
benzylsuccinate synthase (BSS) catalyzes the formation of a C-C bond between toluene and fumarate by a radical mechanism. BSS binds substrates in a buried active site and uses conformational changes to gate access. Both substrates can bind to the BSSalphabetagamma complex
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toluene + fumarate
benzylsuccinate
the enzyme generates enantiospecifically (R)-benzylsuccinate from fumarate and toluene
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r
toluene + fumarate
benzylsuccinate
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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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toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
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additional information
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docking of the substrates into the relaxed active site and structure of the enzyme-product complex, overview. The active site cavity contains two hydrophobic regions, which are involved in interacting with the benzene ring and the protonated carboxyl group, respectively. On the other hand, a hydrophilic portion of the active site cavity binds the deprotonated carboxylic group by a strong electrostatic interaction towards Arg508 and a range of hydrogen bonds. Kinetic isotope effect of 4.0 for [2H] substituents at the methyl group of toluene
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additional information
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docking of the substrates into the relaxed active site and structure of the enzyme-product complex, overview. The active site cavity contains two hydrophobic regions, which are involved in interacting with the benzene ring and the protonated carboxyl group, respectively. On the other hand, a hydrophilic portion of the active site cavity binds the deprotonated carboxylic group by a strong electrostatic interaction towards Arg508 and a range of hydrogen bonds. Kinetic isotope effect of 4.0 for [2H] substituents at the methyl group of toluene
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additional information
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substrate-bound structures of benzylsuccinate synthase, fumarate is secured at the bottom of a long active site cavity with toluene bound directly above it. The two substrates adopt orientations that appear ideal for radical-mediated C-C bond formation, the methyl group of toluene is positioned between fumarate and a cysteine that forms a thiyl radical during catalysis, which is in turn adjacent to the glycine that serves as a radical storage residue. Toluene is held in place by fumarate on one face and tight packing by hydrophobic residues on the other face and sides. These hydrophobic residues appear to become ordered, thus encapsulating toluene, only in the presence of BSSbeta, a small protein subunit that forms a tight complex with BSSalpha, the catalytic subunit. Toluene is activated in anaerobic hydrocarbon degradation, overview. Fumarate binding stabilizes a partially closed conformation in the dimeric BSSalphagamma
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benzylsuccinate
toluene + fumarate
toluene + fumarate
benzylsuccinate
benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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benzylsuccinate
toluene + fumarate
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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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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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toluene + fumarate
benzylsuccinate
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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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toluene + fumarate
benzylsuccinate
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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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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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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
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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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toluene + fumarate
benzylsuccinate
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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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toluene + fumarate
benzylsuccinate
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first step in the anaerobic degradation pathway of toluene
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4.1.99.11 benzylsuccinate synthase
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