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MetaCyc Reaction:

Superclasses: Reactions Classified By Conversion TypeSimple ReactionsChemical Reactions
Reactions Classified By SubstrateSmall-Molecule Reactions

EC Number:

Enzymes and Genes:

Azoarcus sp. T: benzylsuccinate synthaseInferred from experiment: bssA, bssB, bssC
Thauera aromatica: benzylsuccinate synthaseInferred from experiment: bssA, bssB, bssC

In Pathway: toluene degradation to benzoyl-CoA (anaerobic)

The direction shown, i.e. which substrates are on the left and right sides, is in accordance with the Enzyme Commission system.

Mass balance status: Balanced.

Enzyme Commission Primary Name: benzylsuccinate synthase

Enzyme Commission Synonyms: benzylsuccinate fumarate-lyase

Standard Gibbs Free Energy (ΔrG in kcal/mol): -14.21Inferred by computational analysis [Latendresse13]

Enzyme Commission Summary:
The addition of toluene to fumarate to form benzylsuccinate appears to be the initial reaction in anaerobic toluene degradation [Biegert96, Beller97]. This reaction was first demonstrated by in vitro studies conducted with two denitrifying species, Thauera aromatica [Biegert96] and Azoarcus sp. strain T [Beller97]. Since then, benzylsuccinate formation from toluene and fumarate has also been demonstrated in two toluene-mineralizing sulfate-reducing bacteria [Beller97a, Rabus98] and one toluene-utilizing phototrophic [Zengler99] bacterium. Since denitrifiers, sulfate-reducers, and phototrophs represent phylogenetically distant groups of bacteria, this suggests that anaerobic toluene degradation in general may proceed via benzylsuccinate as the initial intermediate.

Citations: [Leuthner98, Beller98]

Gene-Reaction Schematic

Gene-Reaction Schematic

Unification Links: KEGG:R05598, Rhea:10416

Relationship Links: BRENDA:EC:, ENZYME:EC:, IUBMB-ExplorEnz:EC:


Beller97: Beller HR, Spormann AM (1997). "Anaerobic activation of toluene and o-xylene by addition to fumarate in denitrifying strain T." J Bacteriol 1997;179(3);670-6. PMID: 9006019

Beller97a: Beller, HR, Spormann, AM "Benzylsuccinate formation as a means of anaerobic toluene activation by sulfate-reducing strain PRTOL1." Appl Environ Microbiol (1997) 63, 3729-2731.

Beller98: Beller HR, Spormann AM (1998). "Analysis of the novel benzylsuccinate synthase reaction for anaerobic toluene activation based on structural studies of the product." J Bacteriol 180(20);5454-7. PMID: 9765580

Biegert96: Biegert T, Fuchs G, Heider J (1996). "Evidence that anaerobic oxidation of toluene in the denitrifying bacterium Thauera aromatica is initiated by formation of benzylsuccinate from toluene and fumarate." Eur J Biochem 1996;238(3);661-8. PMID: 8706665

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Leuthner98: Leuthner B, Leutwein C, Schulz H, Horth P, Haehnel W, Schiltz E, Schagger H, Heider J (1998). "Biochemical and genetic characterization of benzylsuccinate synthase from Thauera aromatica: a new glycyl radical enzyme catalysing the first step in anaerobic toluene metabolism." Mol Microbiol 1998;28(3);615-28. PMID: 9632263

Rabus98: Rabus, R, Heider, J "Initial reactions of anaerobic metabolism of alkylbenzenes in denitrifying and sulfate-reducing bacteria." Arch Microbiol (1998) 170, 377-384.

Zengler99: Zengler K, Heider J, Rossello-Mora R, Widdel F (1999). "Phototrophic utilization of toluene under anoxic conditions by a new strain of blastochloris sulfoviridis." Arch Microbiol 172(4);204-12. PMID: 10525736

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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