Transformation of Carbon Tetrachloride by Thiol Reductants in the Presence of Quinone Compounds

Doong, Ruey‐an; Chiang, Huai-chih

doi:10.1021/es047956k

Cited by 52 publications

(33 citation statements)

References 35 publications

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“…Electron shuttle-mediated contaminant transformation has been demonstrated for the BTEX compounds (11,39), methyl tert butyl ether (11,12), carbon tetrachloride (9), and metals such as uranium (12,15,25,26,30). The role of electron shuttling in environmental reactions was reviewed by Hernandez and Newman (24).…”

mentioning

confidence: 99%

Microbially Mediated Biodegradation of Hexahydro-1,3,5-Trinitro-1,3,5- Triazine by Extracellular Electron Shuttling Compounds

Kwon

Finneran

2006

Appl Environ Microbiol

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The potential for humic substances to stimulate the reduction of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) was investigated. This study describes a novel approach for the remediation of RDX-contaminated environments using microbially mediated electron shuttling. Incubations without cells demonstrated that reduced AQDS transfers electrons directly to RDX, which was reduced without significant accumulation of the nitroso intermediates. Three times as much reduced AQDS (molar basis) was needed to completely reduce RDX. The rate and extent of RDX reduction differed greatly among electron shuttle/acceptor amendments for resting cell suspensions of Geobacter metallireducens and G. sulfurreducens with acetate as the sole electron donor. AQDS and purified humic substances stimulated the fastest rate of RDX reduction. The nitroso metabolites did not significantly accumulate in the presence of AQDS or humic substances. RDX reduction in the presence of poorly crystalline Fe(III) was relatively slow and metabolites transiently accumulated. However, adding humic substances or AQDS to Fe(III)-containing incubations increased the reduction rates. Cells of G. metallireducens alone reduced RDX; however, the rate of RDX reduction was slow relative to AQDSamended incubations. These data suggest that extracellular electron shuttle-mediated RDX transformation is not organism specific but rather is catalyzed by multiple Fe(III)-and humic-reducing species. Electron shuttle-mediated RDX reduction may eventually become a rapid and effective cleanup strategy in both Fe(III)-rich and Fe(III)-poor environments.

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mentioning

confidence: 99%

Microbially Mediated Biodegradation of Hexahydro-1,3,5-Trinitro-1,3,5- Triazine by Extracellular Electron Shuttling Compounds

Kwon

Finneran

2006

Appl Environ Microbiol

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“…To our knowledge, this is the first demonstration of the utilization of thermodynamic properties of the electron donor to selectively stimulate specific respiratory processes. Although earlier studies have ð5860 mequiv:=6133 mequiv:ÞÂ100 ¼ 95:6% electron balance used AH 2 DS as a reductant for transformation of contaminants, such as hexahydro-1,3,5-trinitro-1,3,5-triazine (Kwon and Finneran, 2006) and carbon tetrachloride (Doong and Chiang, 2005), data presented here indicate that microbial AH 2 DS oxidation can support bioremediative processes as well.…”

Section: Discussionmentioning

confidence: 57%

Thermodynamic targeting of microbial perchlorate reduction by selective electron donors

Trump

Coates

2008

The ISME Journal

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Here we describe 2,6-anthrahydroquinone disulfonate (AH 2 DS) as a model thermodynamically 'targeting' electron donor capable of selectively stimulating respiratory processes relevant to the bioremediation of perchlorate. Pure cultures of Dechloromonas aromatica, Dechloromonas agitata and Azospira suillum, as well as uncharacterized microbial consortia, were capable of stoichiometrically reducing perchlorate to chloride upon oxidation of AH 2 DS to the corresponding quinone 2,6-anthraquinone disulfonate (AQDS). No degradation of the anthraquinone structure was observed, and no organism tested grew by this metabolism. Thermodynamic calculations suggest that AH 2 DS oxidation should support nitrate and perchlorate reduction, whereas sulfate reduction and methanogenesis are predicted to be unfavorable. Mixed community microcosms oxidizing AH 2 DS reduced nitrate and perchlorate, whereas sulfate reduction never occurred. In contrast, microcosms amended with acetate respired nitrate, perchlorate and sulfate, as would be predicted by thermodynamic calculation. Our results suggest that the thermodynamic properties of hydroquinones allow for targeted stimulation of only a subset of potential respiratory processes. This observation could help improve enhanced in situ bioremediation of perchlorate by negating many of the detrimental aspects of biofouling.

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“…Our previous study showed that cysteine in the concentration range 0.5-2 mM is an effective mediator to transfer electrons between Geobacter sulfurreducens and ferrihydrite [27]. High concentrations of cysteine and AQDS have also been used as reductants for the abiotic dechlorination of CT under anoxic conditions [1,17,18]. These results clearly show that both AQDS and cysteine can be used in chemical and biological reactions for degradation of priority pollutants under anaerobic conditions.…”

Section: Introductionmentioning

confidence: 78%

“…The headspace analytical technique was used for the determination of chlorinated hydrocarbons [2,3,17]. The concentrations of CT and byproducts in the headspace of the test bottles were monitored by withdrawing 50 L of gas from the headspace and then injecting into a gas chromatograph (GC, Perkin-Elmer, Autosystem) equipped with an electron capture detector (ECD).…”

Section: Methodsmentioning

confidence: 99%

“…It is generally accepted that the use of electron transfer mediators such as humic acid and quinone moieties can significantly enhance the transformation efficiency and rate of organic contaminants [17][18][19] as well as stimulate the reductive dissolution of Fe(III) oxides [20][21][22]. Current evidence suggests that anthraquinone-2,6-disulfonate (AQDS) is an effective electron shuttle for enhancing the reductive dissolution of Fe(III) oxides by DIRB [20,23,24].…”

Section: Introductionmentioning

confidence: 99%

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Transformation of carbon tetrachloride by biogenic iron species in the presence of Geobacter sulfurreducens and electron shuttles

Maithreepala

Doong

2009

Journal of Hazardous Materials

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Transformation of Carbon Tetrachloride by Thiol Reductants in the Presence of Quinone Compounds

Cited by 52 publications

References 35 publications

Microbially Mediated Biodegradation of Hexahydro-1,3,5-Trinitro-1,3,5- Triazine by Extracellular Electron Shuttling Compounds

Microbially Mediated Biodegradation of Hexahydro-1,3,5-Trinitro-1,3,5- Triazine by Extracellular Electron Shuttling Compounds

Thermodynamic targeting of microbial perchlorate reduction by selective electron donors

Transformation of carbon tetrachloride by biogenic iron species in the presence of Geobacter sulfurreducens and electron shuttles

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