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Literature summary extracted from

  • Szaleniec, M.; Heider, J.
    Modeling of the reaction mechanism of enzymatic radical C-C coupling by benzylsuccinate synthase (2016), Int. J. Mol. Sci., 17, 514 .
    View publication on PubMedView publication on EuropePMC

Activating Compound

EC Number Activating Compound Comment Organism Structure
4.1.99.11 additional information enzyme BSS needs to be posttranslationally activated to the active, radical-containing state by a separate activating enzyme, which is encoded in a common operon with the genes for the BSS subunits and belongs to the family of S-adenosyl-methionine-dependent radical enzymes Thauera aromatica

Application

EC Number Application Comment Organism
4.1.99.11 environmental protection enzyme BSS and the growing number of additional fumarate-adding enzymes have become model cases for environmental processes in contaminated soils and deep anoxic subsediment habitats, and their isotopic preferences and conserved sequences serving as templates for molecular probes are employed as tools for monitoring these processes in situ Thauera aromatica

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
4.1.99.11 Fe2+ one low potential [4Fe4S]-cluster is located in each of the two small subunits Thauera aromatica

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.1.99.11 toluene + fumarate Thauera aromatica
-
benzylsuccinate
-
?

Organism

EC Number Organism UniProt Comment Textmining
4.1.99.11 Thauera aromatica O87943 AND O87944 AND O87942 alpha-, beta-, and gamma-subunit
-

Posttranslational Modification

EC Number Posttranslational Modification Comment Organism
4.1.99.11 additional information enzyme BSS needs to be posttranslationally activated to the active, radical-containing state by a separate activating enzyme, which is encoded in a common operon with the genes for the BSS subunits and belongs to the family of S-adenosyl-methionine-dependent radical enzymes Thauera aromatica

Reaction

EC Number Reaction Comment Organism Reaction ID
4.1.99.11 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 Thauera aromatica

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.1.99.11 additional information 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 Thauera aromatica ?
-
?
4.1.99.11 toluene + fumarate
-
Thauera aromatica benzylsuccinate
-
?
4.1.99.11 toluene + fumarate the enzyme generates enantiospecifically (R)-benzylsuccinate from fumarate and toluene Thauera aromatica benzylsuccinate
-
r

Subunits

EC Number Subunits Comment Organism
4.1.99.11 heterotrimer 1 * 100000 + 1 * 8500 + 1 * 6500, the enzyme consists of three subunits encoded by three different genes and of very different sizes: the large subunit of circa 100 kDa contains the glycyl radical in the active site and presumably carries out the catalysis, whereas the two small subunits of 8.5 and 6.5 kDa each contain a low-potential [4Fe4S]-cluster Thauera aromatica

Synonyms

EC Number Synonyms Comment Organism
4.1.99.11 BSS
-
Thauera aromatica
4.1.99.11 BSSA
-
Thauera aromatica

Cofactor

EC Number Cofactor Comment Organism Structure
4.1.99.11 [4Fe-4S] cluster one low potential [4Fe4S]-cluster is located in each of the two small subunits Thauera aromatica

General Information

EC Number General Information Comment Organism
4.1.99.11 additional information structure homology modeling Thauera aromatica
4.1.99.11 physiological function 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 Thauera aromatica