Anaerobic degradation of m -cresol by Desulfobacterium cetonicum is initiated by formation of 3-hydroxybenzylsuccinate

Müller, Jochen A.; Galushko, Alexander; Kappler, Andreas; Schink, Bernhard

doi:10.1007/s002030050782

Cited by 70 publications

(45 citation statements)

References 41 publications

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“…From mass spectrometric identification of metabolites extracted from culture supernatants of strain OX39, it appears plausible that degradation of toluene, m-xylene, and o-xylene proceeds via fumarate addition to one of the methyl groups to form (methyl)benzylsuccinate. So far, the benzylsuccinate synthase reaction is the only initial reaction reported for degradation of methylated aromatics, e.g., toluene, m-cresol, p-cresol, m-xylene, o-xylene, and 2-methylnaphthalene, by sulfate-reducing, denitrifying, and Fe(III)-reducing bacteria (Biegert et al 1996;Beller and Spormann 1997a,b;Leuthner et al 1998;Krieger et al 1999;Müller et al 1999;Annweiler et al 2000;Müller et al 2001;Kane et al 2002). Further steps in benzylsuccinate degradation detected by enzymatic assays are a CoA-transferase reaction yielding benzylsuccinyl-CoA and a subsequent dehydrogenase reaction leading to phenylitaconyl-CoA (Leutwein and Heider 1999.…”

Section: Discussionmentioning

confidence: 99%

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

Morasch

Schink

Tebbe

et al. 2004

Archives of Microbiology

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118

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A strictly anaerobic bacterium, strain OX39, was isolated with o-xylene as organic substrate and sulfate as electron acceptor from an aquifer at a former gasworks plant contaminated with aromatic hydrocarbons. Apart from o-xylene, strain OX39 grew on m-xylene and toluene and all three substrates were oxidized completely to CO 2 . Induction experiments indicated that o-xylene, m-xylene, and toluene degradation were initiated by different specific enzymes. Methylbenzylsuccinate was identified in supernatants of cultures grown on o-xylene and m-xylene, and benzylsuccinate was detected in supernatants of toluene-grown cells, thus indicating that degradation was initiated in all three cases by fumarate addition to the methyl group. Strain OX39 was sensitive towards sulfide and depended on Fe(II) in the medium as a scavenger of the produced sulfide. 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 hydrocarbonoxidizing bacterium in this genus. Keywords Sulfate reduction · BTEX · Benzylsuccinate synthase · Desulfotomaculum IntroductionPetroleum hydrocarbons are among the most abundant groundwater contaminants and can be found in gasworks plants, landfill leachates, and accidental fuel spills (US-EPA 1999). The mono-aromatic hydrocarbons benzene, toluene, ethylbenzene, and xylene isomers (BTEX) are putatively mutagenic or carcinogenic substances and make-up more than 50% by weight of the water-soluble gasoline fraction (Coleman et al. 1984). Due to their relatively high solubility, they are mobile with the groundwater flow and form contaminant plumes in aquifers. The degradative potential of anaerobic bacteria towards aromatic hydrocarbons in situ was investigated in several studies and a decrease of BTEX compounds could be demonstrated under denitrifying, Fe(III)-reducing, sulfate-reducing, and methanogenic conditions (Dolfing et al. 1990;Kazumi et al. 1997;Reinhard et al. 1997;Gieg et al. 1999;Phelps and Young 2001). Numerous anaerobic bacterial cultures have been enriched in the past, and pure strains have been isolated. Of all BTEX compounds, toluene has been studied most extensively with respect to its anaerobic degradation. Pure cultures of toluene-degrading bacteria that use NO 3 -, Fe(III), or SO 4 2-as electron acceptors have been isolated (Lovley and Lonergan 1990;Rabus et al. 1993;Seyfried et al. 1994;Zhou et al. 1995;Beller et al. 1996). Under anoxic conditions, degradation of toluene proceeds via addition of fumarate to the methyl group (Biegert et al. 1996;Beller and Spormann 1997b;Leuthner et al. 1998;Rabus and Heider 1998;Kane et al. 2002).Consumption of o-xylene was discovered simultaneously with toluene degradation in methanogenic consortia (Edwards and Grbic-Galic 1994). Later, transformation of o-xylene to o-methyl homologs of benzylsuccinate by toluene-degrading strains was reported; however, no further oxidation steps could be observed (Beller and Spormann...

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Section: Discussionmentioning

confidence: 99%

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

Morasch

Schink

Tebbe

et al. 2004

Archives of Microbiology

Self Cite

118

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“…Similar operons may be present in other strains, as the novel benzylsuccinate synthase reaction, catalyzing the addition of fumarate to toluene (110,181), may also be involved in the metabolism of xylenes (349,444,445), alkylnaphthalenes (20,23), n-hexadecane (497), and n-dodecane (351). For example, dodecylsuccinic acids were detected from a sulfate-reducing enrichment culture growing on n-dodecane (351), and an nhexane-utilizing denitrifying bacterium with a protein similar to BssC has been isolated from the toluene-degrading denitrifying bacteria (664).…”

Section: Anaerobic Hydrocarbon Metabolismmentioning

confidence: 91%

Recent Advances in Petroleum Microbiology

Hamme¹,

Singh

Ward

2003

Microbiol Mol Biol Rev

1,203

640

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Recent advances in molecular biology have extended our understanding of the metabolic processes related to microbial transformation of petroleum hydrocarbons. The physiological responses of microorganisms to the presence of hydrocarbons, including cell surface alterations and adaptive mechanisms for uptake and efflux of these substrates, have been characterized. New molecular techniques have enhanced our ability to investigate the dynamics of microbial communities in petroleum-impacted ecosystems. By establishing conditions which maximize rates and extents of microbial growth, hydrocarbon access, and transformation, highly accelerated and bioreactor-based petroleum waste degradation processes have been implemented. Biofilters capable of removing and biodegrading volatile petroleum contaminants in air streams with short substrate-microbe contact times (<60 s) are being used effectively. Microbes are being injected into partially spent petroleum reservoirs to enhance oil recovery. However, these microbial processes have not exhibited consistent and effective performance, primarily because of our inability to control conditions in the subsurface environment. Microbes may be exploited to break stable oilfield emulsions to produce pipeline quality oil. There is interest in replacing physical oil desulfurization processes with biodesulfurization methods through promotion of selective sulfur removal without degradation of associated carbon moieties. However, since microbes require an environment containing some water, a two-phase oil-water system must be established to optimize contact between the microbes and the hydrocarbon, and such an emulsion is not easily created with viscous crude oil. This challenge may be circumvented by application of the technology to more refined gasoline and diesel substrates, where aqueous-hydrocarbon emulsions are more easily generated. Molecular approaches are being used to broaden the substrate specificity and increase the rates and extents of desulfurization. Bacterial processes are being commercialized for removal of H2S and sulfoxides from petrochemical waste streams. Microbes also have potential for use in removal of nitrogen from crude oil leading to reduced nitric oxide emissions provided that technical problems similar to those experienced in biodesulfurization can be solved. Enzymes are being exploited to produce added-value products from petroleum substrates, and bacterial biosensors are being used to analyze petroleum-contaminated environments

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“…An activation of benzoate via a CoA-transferase was discussed for a sulfate-reducing bacterium (Kuever et al 1993), however, without experimental proof. Involvement of CoA-transferases acting on ω-carboxy groups of side chains of aromatic compounds has been reported for the anaerobic degradation of toluene (Leutwein and Heider 1999) and m-cresol (Müller et al 1999). 3-Hydroxybenzoyl-CoA was reductively dehydroxylated to benzoyl-CoA, as measured in cell-free extracts with cob(I)alamin as the low-potential electron donor.…”

Section: Benzoyl-coa Reductasementioning

confidence: 99%

Initial steps in the fermentation of 3-hydroxybenzoate by Sporotomaculum hydroxybenzoicum

Müller

Schink

2000

Archives of Microbiology

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The anaerobic bacterium Sporotomaculum hydroxybenzoicum ferments 3-hydroxybenzoate to acetate, butyrate, and CO 2 . 3-Hydroxybenzoate was activated to 3-hydroxybenzoyl-CoA in a CoA-transferase reaction with acetyl-CoA or butyryl-CoA as CoA donors. 3-Hydroxybenzoyl-CoA was reductively dehydroxylated, forming benzoyl-CoA. This reaction was measured in cell-free extracts with cob(I)alamin as low-potential electron donor. No evidence was obtained that cob(I)alamin is the physiological electron donor; however, inhibitor studies indicated involvement of a strong nucleophile in the reaction. Benzoate was degraded by dense cell suspensions without a lag phase until an in situ ∆G′ value <-25 kJ mol -1 was reached. Benzoyl-CoA reductase was not detected. Enzyme activities for all reaction steps from glutaryl-CoA to butyryl-CoA, and ATP formation via acetate kinase were detected in cell-free extracts. GlutaconylCoA decarboxylase is likely to act as a primary sodium ion pump.

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Anaerobic degradation of m -cresol by Desulfobacterium cetonicum is initiated by formation of 3-hydroxybenzylsuccinate

Cited by 70 publications

References 41 publications

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

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

Recent Advances in Petroleum Microbiology

Initial steps in the fermentation of 3-hydroxybenzoate by Sporotomaculum hydroxybenzoicum

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