Concomitant aerobic biodegradation of benzene and thiophene

Dyreborg, Søren; Arvin, Erik; Broholm, Kim

doi:10.1002/etc.5620170512

Cited by 9 publications

(1 citation statement)

References 20 publications

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“…1 Thiophenes are liberated into the environment during cooking processes and the combustion of fossil fuels. 2 Examples of naturally occurring 2-substituted thiophenes include 2-methylthiophene 1B, 2-ethylthiophene 1C and 2-propylthiophene (from yeast extract). 3 Animal (eucaryotic) metabolic pathways, adopted for the monosubstituted thienyl moiety (Th), are exemplified by the drugs methapyrilene 2, tenidap 3, tienilic acid 4 and temocillin 5.…”

Section: Introductionmentioning

confidence: 99%

Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation

et al. 2003

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Toluene dioxygenase (TDO)-catalysed sulfoxidation, using Pseudomonas putida UV4, was observed for the thiophene substrates 1A-1N. The unstable thiophene oxide metabolites, 6A-6G, 6K-6N, spontaneously dimerised yielding the corresponding racemic disulfoxide cycloadducts 7A-7G, 7K-7N. Dimeric or crossed [4 + 2] cycloaddition products, derived from the thiophene oxide intermediates 6A and 6D or 6B and 6D, were found when mixtures of thiophene substrates 1A and 1D or 1B and 1D were biotransformed. The thiophene sulfoxide metabolite 6B was also trapped as cycloadducts 17 or 18 using stable dienophiles. Preferential dioxygenase-catalysed oxidation of the substituent on the thiophene ring, including exocyclic sulfoxidation (1H-1J) and cis-dihydroxylation of a phenyl substituent (1G and 1N), was also observed. An enzyme-catalysed deoxygenation of a sulfoxide in P. putida UV4 was noticed when racemic disulfoxide cyclo-adducts 7A, 7B and 7K were converted to the corresponding enantioenriched monosulfoxides 8A, 8B and 8K via a kinetic resolution process. The parent thiophene 1A and the 3-substituted thiophenes 1K-1N were also found to undergo ring dihydroxylation yielding the cis/trans-dihydrodiol metabolites 9A and 9K-9N. Evidence is provided for a dehydrogenase-catalysed desaturation of a heterocyclic dihydrodiol (9Kcis/9Ktrans) to yield the corresponding 2,3-dihydroxythiophene (24) as its preferred thiolactone tautomer (23). A simple model to allow prediction of the structure of metabolites, formed from TDO-catalysed bacterial oxidation of thiophene substrates 1, is presented.

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Section: Introductionmentioning

confidence: 99%

Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation

et al. 2003

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Microbial Degradation of Tar Oil Compounds under Different Redox Conditions

Mundt

Althoff

Dott

et al. 2003

Acta hydrochim. hydrobiol.

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The microbial transformation of typical tar oil compounds such as acridine, benzo(b)thiophene, dibenzofuran, indane, and indene under different redox conditions was investigated in microcosm studies. Under aerobic conditions the inherent contamination in polluted soil as well as the added N-, S-, O-heterocyclic and homocyclic compounds were transformed predominantly apart from thiophene. 1-Indanone was detected by RP-HPLC-DAD and GC-MS as an intermediate metabolite from indane and indene. Under nitrate and sulfate reducing conditions indane, benzo(b)thiophene, and dibenzofuran were transformed in assays with the polluted soil samples from well B 65 and B 66 within 426 days, whereas they were persistent in assays with the highly polluted soil B 67. All heterocyclic and homocyclic compounds added to the non-contaminated soil from well B 85 were not degraded under nitrate and sulfate reducing conditions, too. The results indicate that for the decision, wether natural attenuation can be implemented in the remediation of contaminated site, in addition to BTEX and PAHs especially the fate of further tar oil compounds in anoxic aquifers has to be considered. Mikrobieller Abbau von Teerölbegleitstoffen unter verschiedenen Redox-BedingungenDer mikrobielle Umsatz von typischen Teerölsubstanzen, wie Acridin, Benzo(b)thiophen, Dibenzofuran, Indan und Inden, wurde unter verschiedenen Redoxbedingungen in Mikrokosmen untersucht. Unter aeroben Bedingungen wurde sowohl in belasteten Bodenproben die inhärente Kontamination als auch in unbelasteten Bodenproben die zudotierten heterocyclischen und homocyclischen Verbindungen außer Thiophen überwiegend umgesetzt. 1-Indanon wurde als ein intermediärer Metabolit von Indan und Inden mittels RP-HPLC-DAD und GC-MS nachgewiesen. Unter denitrifizierenden und desulfurizierenden Bedingungen wurden Indan, Benzo(b)thiophen und Dibenzofuran in Ansätzen mit den belasteten Bodenproben von Brunnen B 65 und B 66 innerhalb von 426 Tagen umgesetzt, während sie in denen mit dem hoch belasteten Boden B 67 persistent blieben. Alle heterocyclischen und homocyclischen Stoffe, die den Versuchen mit unbelastetem Boden von Brunnen B 85 zugesetzt wurden, wurden ebenfalls nicht abgebaut. Die Ergebnisse zeigen, dass für die Entscheidung, ob Natural Attenuation an einem Standort implementiert werden kann, neben BTEX und PAK besonders der Verbleib weiterer Teerölverbindungen in anaeroben Aquifern zu prüfen ist.

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Determination of PCB Elimination Coefficients in Round Goby and Tubenose Goby

Sun

Johnson

Drouillard

2016

Bull Environ Contam Toxicol

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Whole-body elimination coefficients of polychlorinated biphenyls (PCBs) were determined in two Great Lakes invasive fish species, round goby (Neogobius melanostomus) and tubenose goby (Proterorhinus semilunaris). Elimination rates were determined for a set of model PCB congeners (n = 12 congeners) dosed to fish by intraperitoneal injection and allowed to depurate at a temperature of 21.4°C for 90 days. Eight PCBs (PCB 6, 21, 57, 62, 68, 89, 112 and 125) exhibited significant elimination by round goby and had corresponding half lives ranging from 13 to 39.8 days. For tubenose goby, four congeners (PCBs 21, 57, 62 and 68) exhibited significant elimination with half lives in the range from 18.8 to 48.8 days. Whole-body elimination rate coefficients were significantly higher for round gobies compared to tubenose goby. In both cases, PCB elimination rate coefficients were negatively related to chemical log KOW.

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Concomitant aerobic biodegradation of benzene and thiophene

Cited by 9 publications

References 20 publications

Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation

Dioxygenase-catalysed oxidation of monosubstituted thiophenes: sulfoxidation versus dihydrodiol formation

Microbial Degradation of Tar Oil Compounds under Different Redox Conditions

Determination of PCB Elimination Coefficients in Round Goby and Tubenose Goby

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