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

Altenschmidt, Uwe; Fuchs, Georg

doi:10.1128/jb.174.14.4860-4862.1992

Cited by 42 publications

(30 citation statements)

References 17 publications

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“…In particular, none of the labeled compounds derived from ['4C]toluene comigrated with benzyl alcohol or benzaldehyde on TLC or HPLC, as had been suggested by earlier investigations (Altenschmidt and Fuchs, 1992). Standards of both compounds could be detected by fluorescence quenching after TLC, despite their volatility.…”

Section: Anaerobic Oxidation Of Toluene By Cell Extracts and Requiremmentioning

confidence: 51%

“…This proposal has come from reports of accumulation of benzaldehyde and/or benzyl alcohol from toluene in cell suspensions. Toluene metabolism was either blocked by the inhibitor iodoacetamide (Altenschmidt and Fuchs, 1992) or slowed down by performing the reaction at 5°C (Seyfried et al, 1994). These experiments had been done with very weakly 14C-labeled toluene (AltenSchmidt and Fuchs, 1992) or with unlabeled toluene in a concentration (6 mM) that is already toxic for 7: aromatica (Seyfried et al, 1994).…”

mentioning

confidence: 99%

“…Toluene metabolism was either blocked by the inhibitor iodoacetamide (Altenschmidt and Fuchs, 1992) or slowed down by performing the reaction at 5°C (Seyfried et al, 1994). These experiments had been done with very weakly 14C-labeled toluene (AltenSchmidt and Fuchs, 1992) or with unlabeled toluene in a concentration (6 mM) that is already toxic for 7: aromatica (Seyfried et al, 1994). The conditions used were not physiological and in both cases identification of the products was based on cochromatography in only one HPLC eluant system.…”

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confidence: 99%

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Evidence That Anaerobic Oxidation of Toluene in the Denitrifying Bacterium Thauera aromatica is Initiated by Formation of Benzylsuccinate from Toluene and Fumarate

Biegert

Fuchs

Heider

1996

European Journal of Biochemistry

278

257

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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 cells: Cell‐free extracts oxidized [14C]toluene to [14C]benzoyl‐CoA via several radioactive intermediates. This reaction was strictly dependent on the presence of fumarate, coenzyme A and nitrate as electron acceptor; acetyl‐CoA and ATP were not necessary for the reaction. The first product formed in vitro was benzylsuccinate; (2H8)toluene was converted to (2H7)benzylsuccinate. Formation of benzylsuccinate from toluene was independent of coenzyme A and nitrate, but it required the presence of fumarate. Other tricarboxylic acid cycle intermediates were converted to fumarate in cell extracts and therefore could partially substitute for fumarate. [14C]Benzylsuccinate was oxidized further to [14C]benzoyl‐CoA and [14C]benzoate in cell extracts if coenzyme A and nitrate were present. No benzyl alcohol and benzaldehyde and no phenylpropionate could be detected as intermediates. In isotope trapping experiments with cell suspensions, two intermediates from [14C]toluene were detected, benzoate and benzylsuccinate. This corroborates the sequence of reactions deduced from in vitro experiments. A hypothetical degradation pathway for the anaerobic oxidation of toluene to benzoyl‐CoA via an initial addition of fumarate to the methyl group of toluene and following β‐oxidation of the benzylsuccinate formed is suggested.

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Section: Anaerobic Oxidation Of Toluene By Cell Extracts and Requiremmentioning

confidence: 51%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Evidence That Anaerobic Oxidation of Toluene in the Denitrifying Bacterium Thauera aromatica is Initiated by Formation of Benzylsuccinate from Toluene and Fumarate

Biegert

Fuchs

Heider

1996

European Journal of Biochemistry

278

257

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“…Benzaldehyde is known to be an oxidative product of the biodegradation of toluene and, in this project, served as a convenient marker for biodegradation. [32][33][34] The biplot generated from PCA for soil samples collected in the Fall is shown in Figure 3.…”

Section: Microbial Degradation Studiesmentioning

confidence: 99%

Microbial degradation of gasoline in soil: Effect of season of sampling

Turner

Pichtel

Rodenas

et al. 2015

Forensic Science International

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In cases where fire debris contains soil, microorganisms can rapidly and irreversibly alter the chemical composition of any ignitable liquid residue that may be present. In this study, differences in microbial degradation due to the season in which the sample is collected was examined. Soil samples were collected from the same site during Fall, Winter, Spring and Summer and the degradation of gasoline was monitored over 30 days. Predominant viable bacterial populations enumerated using real-time PCR and reverse transcriptase polymerase chain reaction (RT-PCR) enumeration revealed the predominant viable bacterial genera to be Alcaligenes, Bacillus, and Flavobacterium. Overall, the compounds most vulnerable to microbial degradation are the n-alkanes, followed by the mono-substituted alkylbenzenes (e.g., toluene, ethylbenzene, propylbenzene and isopropylbenzene). Benzaldehyde (a degradation product of toluene) was also identified as a marker for the extent of biodegradation.Ultimately, it was determined that soil collected during an unusually hot and dry summer exhibited the least degradation with little to no change in gasoline for up to 4 days, readily detectable n-alkanes for up to 7 days and relatively high levels of resilient compounds such as

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“…However, the most common first step in the catabolism of toluene is reported as the addition of fumarate onto the toluene methyl group to form benzylsuccinate, which is further metabolized to benzoyl-CoA, via a proposed pathway shown in Figure 2.6. Another possible pathway, suggested by Altenschmidt and Fuchs (1992), includes formation of benzyl alcohol as an initial intermediate followed by benzaldehyde, benzoate and finally to benzoyl-CoA. Heider et al, 1998).…”

Section: Anaerobic Btex Metabolic Pathwaysmentioning

confidence: 99%

In situ Groundwater Remediation Using Enricher Reactor – Permeable Reactive Biobarrier

Kasi¹,

McEvoy²,

Padmanabhan³

et al. 2010

proc water environ fed

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Permeable reactive biobarrier (PRBB) is a flow-through zone where microorganisms degrade contaminants in groundwater. Discontinuous presence of contaminants in groundwater causes performance loss of a PRBB in removing the target contaminant. A novel enricher reactor (ER) -PRBB system was developed to treat groundwater with contaminants that reappear after an absence period. ER is an offline reactor for enriching contaminant degraders, which were used for augmenting PRBB to maintain its performance after a period of contaminant absence. The ER-PRBB concept was initially applied to remove benzene that reappeared after absence periods of 10 and 25 days. PRBBs without ER augmentation experienced performance losses of up to 15% higher than ER-PRBBs.The role of inducer compounds in the ER to enrich bacteria that can degrade a mixture of benzene, toluene, ethylbenzene, and xylene (BTEX) was investigated with an objective to minimize the use of toxic chemicals as inducers. Three inducer types were studied: individual BTEX compounds, BTEX mixture, and benzoate (a non toxic and a common intermediate for BTEX biodegradation). Complete BTEX removal was observed for degraders enriched on all three inducer types; however, the removal rates were dependent on the inducer type. Degraders enriched on toluene and BTEX had the highest degradation rates for BTEX of 0.006 to 0.014 day -1 and 0.006 to 0.012 day -1 , respectively, while degraders enriched on benzoate showed the lowest degradation rates of 0.004 to 0.009 day -1 .The ER-PRBB technique was finally applied to address the performance loss of a PRBB due to inhibition interactions among BTEX, when the mixture reappeared after a iv 10 day absence period. The ER-PRBBs experienced minimal to no performance loss, while PRBBs without ER augmentation experienced performance losses between 11% and 35%. Presence of ethanol during the BTEX absence period increased the performance loss of PRBB for benzene removal. PRBBs augmented with degraders enriched on toluene alone overcame the inhibition interaction between benzene and toluene indicating that toluene can be used as a single effective inducer in an ER. The ER-PRBB was demonstrated to be a promising remediation technique and has potential for applications to a wide range of organic contaminants.v ACKNOWLEDGEMENTS

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

Cited by 42 publications

References 17 publications

Evidence That Anaerobic Oxidation of Toluene in the Denitrifying Bacterium Thauera aromatica is Initiated by Formation of Benzylsuccinate from Toluene and Fumarate

Evidence That Anaerobic Oxidation of Toluene in the Denitrifying Bacterium Thauera aromatica is Initiated by Formation of Benzylsuccinate from Toluene and Fumarate

Microbial degradation of gasoline in soil: Effect of season of sampling

In situ Groundwater Remediation Using Enricher Reactor – Permeable Reactive Biobarrier

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