Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

MetaCyc Reaction: 4.1.99.11

Superclasses: Reactions Classified By Conversion Type Simple Reactions Chemical Reactions
Reactions Classified By Substrate Small-Molecule Reactions

EC Number: 4.1.99.11

Enzymes and Genes:
benzylsuccinate synthase Inferred from experiment : bssA , bssB , bssC ( Thauera aromatica )
benzylsuccinate synthase Inferred from experiment : bssA , bssB , bssC ( Azoarcus sp. T )

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 Inferred 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: ?

Unification Links: KEGG:R05598 , Rhea:10416

Relationship Links: BRENDA:EC:4.1.99.11 , ENZYME:EC:4.1.99.11 , IUBMB-ExplorEnz:EC:4.1.99.11


References

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
Page generated by SRI International Pathway Tools version 18.5 on Tue Nov 25, 2014, BIOCYC13A.