|Superclasses:||Reactions Classified By Conversion Type → Simple Reactions → Chemical Reactions|
|Reactions Classified By Substrate → Small-Molecule Reactions|
EC Number: 220.127.116.11
In Pathway: toluene degradation to benzoyl-CoA (anaerobic)
The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, 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): -14.21 [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.
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
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
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
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