Evidence that anaerobic oxidation of toluene in the denitrifying bacterium Thauera aromatica is initiated by formation of benzylsuccinate from toluene and fumarate.

@article{Biegert1996EvidenceTA,
  title={Evidence that anaerobic oxidation of toluene in the denitrifying bacterium Thauera aromatica is initiated by formation of benzylsuccinate from toluene and fumarate.},
  author={Thomas Biegert and Georg Fuchs and Johann Heider},
  journal={European journal of biochemistry},
  year={1996},
  volume={238 3},
  pages={
          661-8
        }
}
Toluene is degraded anoxically to CO2 by the denitrifying bacterium Thauera aromatica. Toluene first becomes oxidized to benzoyl-CoA by O2-independent reactions. Benzoyl-CoA is then reduced to non-aromatic products by benzoyl-CoA reductase. We set out to study the reactions employed for the initial activation of toluene and its oxidation to the level of benzoate. Evidence is provided for a novel way of toluene degradation based on experiments with cell-free extracts and with whole toluene-grown… 
View on PubMed
doi.org
281 Citations
Highly Influential Citations
23
Background Citations
143
Methods Citations
24
Results Citations
9

281 Citations

Anaerobic toluene-catabolic pathway in denitrifying Thauera aromatica: activation and beta-oxidation of the first intermediate, (R)-(+)-benzylsuccinate.

The authors show by experiments with cell extracts of toluene-grown T. aromatica that the pathway of benzylsuccinate oxidation requires activation of the free acid to a CoA-thioester, catalysed by a toLUene-induced, reversible succinyl-CoA-dependent CoA -transferase.

Anaerobic activation of toluene and o-xylene by addition to fumarate in denitrifying strain T

Use of deuterium-labeled toluene and gas chromatography-mass spectrometry indicated that the H atom abstracted from the toLUene methyl group during addition to fumarate was retained in the succinyl moiety of benzylsuccinate.

Initial reactions of anaerobic metabolism of alkylbenzenes in denitrifying and sulfate-reducing bacteria

Abstract The initial activation reactions of anaerobic oxidation of the aromatic hydrocarbons toluene and ethylbenzene were investigated in cell extracts of a toluene-degrading, sulfate-reducing…

Anaerobic Toluene Catabolism of Thauera aromatica: the bbs Operon Codes for Enzymes of β Oxidation of the Intermediate Benzylsuccinate

ABSTRACT The pathway of anaerobic toluene oxidation to benzoyl coenzyme A (benzoyl-CoA) consists of an initial reaction catalyzed by benzylsuccinate synthase, a glycyl radical enzyme adding the…

(R)-Benzylsuccinyl-CoA dehydrogenase of Thauera aromatica, an enzyme of the anaerobic toluene catabolic pathway

(R)-Benzylsuccinyl-CoA dehydrogenase was detected as a specifically substrate-induced protein in toluene- and m-xylene-grown cells of several bacterial species, using enzyme activity and immunological detection.

Initiation of Anaerobic Degradation of p-Cresol by Formation of 4-Hydroxybenzylsuccinate inDesulfobacterium cetonicum

In cell extracts, the formation of 4-hydroxybenzylsuccinate from p-cresol and fumarate was detected at an initial rate of 0.57 nmol min(-1) (mg of protein)(-1), which indicated that the methyl group of p- cresol is activated by addition to fomarate, analogous to anaerobic toluene, m-xylene, and m-c Resol degradation.

Succinyl-CoA:(R)-Benzylsuccinate CoA-Transferase: an Enzyme of the Anaerobic Toluene Catabolic Pathway in Denitrifying Bacteria

The deduced amino acid sequences resemble those of only two other characterized CoA-transferases, oxalyl-CoA:formate Co a-transferase and (E)-cinnamoyl-Co a:(R)-phenyllactate Coa- transferase, which represent a new family of CoA -transferases.

Methanogenic toluene metabolism: community structure and intermediates.

The results suggest that toluene is activated by fumarate addition, presumably by the dominant Clostridiales.

Degradation of o-xylene and m-xylene by a novel sulfate-reducer belonging to the genus Desulfotomaculum

Analysis of the PCR-amplified 16S rRNA gene revealed that strain OX39 affiliates with the gram-positive endospore-forming sulfate reducers of the genus Desulfotomaculum and is the first hydrocarbon-oxidizing bacterium in this genus.

Enzymatic reactions in anaerobic 2-methylnaphthalene degradation by the sulphate-reducing enrichment culture N 47.

...

References

SHOWING 1-10 OF 18 REFERENCES

Initial reactions in the anaerobic oxidation of toluene and m-xylene by denitrifying bacteria

During anaerobic growth with toluene strains T and K172 produced two transformation products, benzylsuccinate and benzylfumarate, and about 0.5% of the toLUene carbon was converted to these products.

Anaerobic degradation of toluene in denitrifying Pseudomonas sp.: indication for toluene methylhydroxylation and benzoyl-CoA as central aromatic intermediate

The data conclusively show anaerobic growth of a pure culture on tolucne and suggest that toluene is anaerobically degraded via benzoyl-CoA and imply that water functions as the source of the hydroxyl group in a toLUene methylhydroxylase reaction.

Metabolites formed during anaerobic transformation of toluene and o-xylene and their proposed relationship to the initial steps of toluene mineralization

The main pathway for toLUene oxidation to carbon dioxide involves a mechanism similar to that for the formation of the metabolites and involves an attack of the methyl group of toluene by acetyl-coenzyme A.

Complete oxidation of toluene under strictly anoxic conditions by a new sulfate-reducing bacterium

Results do not support a degradation of toluene via one of the cresols or methylbenzoates, benzyl alcohol, or phenylacetate as free intermediate, and Sequencing of 16S rRNA revealed a relationship to the metabolically dissimilar genus Desulfobacter and on a deeper level to the genus Des sulfurobacterium.

Enzymatic reduction of benzoyl-CoA to alicyclic compounds, a key reaction in anaerobic aromatic metabolism.

The anaerobic metabolism of these compounds has been shown in this organism to proceed directly via benzoyl-CoA rather than via free benzoate, suggesting that the reduction reaction is more complex.

Anaerobic degradation of toluene by a denitrifying bacterium

O-xylene was transformed to a metabolite in the presence of toluene but did not serve as the sole source of carbon for growth of strain T1, which was distinct from other bacteria that oxidize toLUene anaerobically, but it may utilize a similar biochemical pathway of oxidation.

Anaerobic Oxidation of Toluene, Phenol, and p-Cresol by the Dissimilatory Iron-Reducing Organism, GS-15

The metabolism of toluene, phenol, and p-cresol by GS-15 provides a model for how aromatic hydrocarbons and phenols may be oxidized with the reduction of Fe(III) in contaminated aquifers and petroleum-containing sediments.

Anaerobic toluene oxidation to benzyl alcohol and benzaldehyde in a denitrifying Pseudomonas strain

The denitrifying Pseudomonas strain K172 was grown with a generation time of 6 h to a cell density of 0.4 g (dry weight) per liter with toluene and nitrate as substrates. We found that anaerobic cell…

Rapid Microbial Mineralization of Toluene and 1,3-Dimethylbenzene in the Absence of Molecular Oxygen

The results suggest that aromatic hydrocarbons present in anoxic environments such as lake sediments, sludge digestors, and groundwater infiltration zones from landfills and polluted rivers are not necessarily persistent but may be mineralized in the absence of molecular oxygen.

Microbial degradation of toluene under sulfate-reducing conditions and the influence of iron on the process

Toluene degradation occurred concomitantly with sulfate reduction in anaerobic microcosms inoculated with contaminated subsurface soil from an aviation fuel storage facility near the Patuxent River and in enrichment cultures in which toluene was the sole carbon source.