Diones, sulfoxides, and sulfones from the aerobic cometabolism of methylbenzothiophenes by Pseudomonas strain BT1

Saftic, Sanja; Fedorak, Phillip M.; Andersson, Jan T.

doi:10.1021/es00033a007

Cited by 54 publications

(56 citation statements)

References 20 publications

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“…However, no bacterial strain has been found to grow on benzothiophenes as the sole carbon source, and all reported biotransformations of benzothiophenes are based on cometabolism. Attacks on the thiophene ring of benzothiophenes lead to the formation of sulfoxides and sulfones, or to ring opening and the formation of 2-mercaptomandelaldehyde and 2-mercaptophenylglyoxalate [158][159][160]. Catabolism of dibenzothiophene is catalyzed by distinct enzymes in two pathways (Scheme 7).…”

Section: Alicyclic Hydrocarbonsmentioning

confidence: 99%

Aerobic Degradation of Petroleum Components by Microbial Consortia

Aa¹,

Essien²

2014

J Pet Environ Biotechnol

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This article is a state-of-the-art review on the aerobic degradation of petroleum components that are commonly found in the environment. Numerous microorganisms have been isolated and their phylogeny and metabolic capacity to degrade a variety of aliphatic and aromatic hydrocarbons have been demonstrated. This review focuses on recent progress on how microbes degrade hydrocarbons and heteroaromatic components of petroleum contaminants directed towards better understanding of the aerobic degradation processes and their exploitation for bioremediation. The phylogenetic diversity of the oil-degrading microbes was also discussed.

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Section: Alicyclic Hydrocarbonsmentioning

confidence: 99%

Aerobic Degradation of Petroleum Components by Microbial Consortia

Aa¹,

Essien²

2014

J Pet Environ Biotechnol

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“…Six metabolites of BT were detected by GC-MS: BTO 2 and 2-mercaptobenzoic acid were identified by comparison of their retention times and mass spectra with those of authentic compounds; 2-hydroxybenzothiophene, 3-hydroxybenzothiophene, benzothiophene-2,3-dione and BTO were identified by comparison of their mass spectra with published data (Saftić et al, 1992;Eaton & Nitterauer, 1994;Kropp et al, 1994b;Gilbert et al, 1998). These results indicate that strain XLDN2-5 is able to catalyse lateral dioxygenation and S oxidation on the thiophene ring of BT.…”

Section: Microbial Transformation Of Benzothiophenesmentioning

confidence: 99%

“…However, no bacterial strain has been found that is able to grow on benzothiophenes as the sole carbon source, and all reported biotransformations of benzothiophenes are based on cometabolism. Attacks on the thiophene ring of benzothiophenes lead to the formation of sulfoxides and sulfones, or to ring opening and the formation of 2-mercaptomandelaldehyde and 2-mercaptophenylglyoxalate (Saftić et al, 1992;Eaton & Nitterauer, 1994;Gilbert et al, 1998). Interestingly, it has been reported that BTO is trapped as a Diels-Alder-type disulfoxide cycloadduct, which yields (Kropp et al, 1994b).…”

Section: Introductionmentioning

confidence: 99%

Microbial transformation of benzothiophenes, with carbazole as the auxiliary substrate, by Sphingomonas sp. strain XLDN2-5

Gai

Wang

et al. 2008

Microbiology

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“…Analyses of acid extracts of laboratory cultures biodegrading benzothiophene, methylbenzothiophene, DBT, and methylDBTs produce a variety of 2,3-diones (5,15,33,34,39,40). When benzothiophene-2,3-dione and 7-methylbenzothiophene-2,3-dione were combined in liquid medium, seven different disulfides were formed (8) by the mechanism shown in Fig.…”

Section: Discussionmentioning

confidence: 99%

Aerobic Biodegradation of 2,2′-Dithiodibenzoic Acid Produced from Dibenzothiophene Metabolites

Young

Cheng

Fedorak

2006

Appl Environ Microbiol

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Dibenzothiophene is a sulfur heterocycle found in crude oils and coal. The biodegradation of dibenzothiophene through the Kodama pathway by Pseudomonas sp. strain BT1d leads to the formation of three disulfides: 2-oxo-2-(2-thiophenyl)ethanoic acid disulfide, 2-oxo-2-(2-thiophenyl)ethanoic acid-2-benzoic acid disulfide, and 2,2-dithiodibenzoic acid. When provided as the carbon and sulfur source in liquid medium, 2,2-dithiodibenzoic acid was degraded by soil enrichment cultures. Two bacterial isolates, designated strains RM1 and RM6, degraded 2,2-dithiodibenzoic acid when combined in the medium. Isolate RM6 was found to have an absolute requirement for vitamin B 12 , and it degraded 2,2-dithiodibenzoic acid in pure culture when the medium was supplemented with this vitamin. Isolate RM6 also degraded 2,2-dithiodibenzoic acid in medium containing sterilized supernatants from cultures of isolate RM1 grown on glucose or benzoate. Isolate RM6 was identified as a member of the genus Variovorax using the Biolog system and 16S rRNA gene analysis. Although the mechanism of disulfide metabolism could not be determined, benzoic acid was detected as a transient metabolite of 2,2-dithiodibenzoic acid biodegradation by Variovorax sp. strain RM6. In pure culture, this isolate mineralized 2,2-dithiodibenzoic acid, releasing 59% of the carbon as carbon dioxide and 88% of the sulfur as sulfate.

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Diones, sulfoxides, and sulfones from the aerobic cometabolism of methylbenzothiophenes by Pseudomonas strain BT1

Cited by 54 publications

References 20 publications

Aerobic Degradation of Petroleum Components by Microbial Consortia

Aerobic Degradation of Petroleum Components by Microbial Consortia

Microbial transformation of benzothiophenes, with carbazole as the auxiliary substrate, by Sphingomonas sp. strain XLDN2-5

Aerobic Biodegradation of 2,2′-Dithiodibenzoic Acid Produced from Dibenzothiophene Metabolites

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