Bacterial degradation of chlorophenols and their derivatives

Arora, Pankaj; Bae, Hyeun‐Jong

doi:10.1186/1475-2859-13-31

Cited by 187 publications

(127 citation statements)

References 133 publications

(192 reference statements)

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“…This oxidative dehalogenation is often catalyzed by flavin-dependent monooxygenases (20). These oxygenases include both types of monooxygenases, those that utilize a single protein as well as those that utilize two proteins.…”

mentioning

confidence: 99%

Kinetic Mechanism of the Dechlorinating Flavin-dependent Monooxygenase HadA

Pimviriyakul

Thotsaporn

Sucharitakul

et al. 2017

Journal of Biological Chemistry

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Edited by F. Peter GuengerichThe accumulation of chlorophenols (CPs) in the environment, due to their wide use as agrochemicals, has become a serious environmental problem. These organic halides can be degraded by aerobic microorganisms, where the initial steps of various biodegradation pathways include an oxidative dechlorinating process in which chloride is replaced by a hydroxyl substituent. Harnessing these dechlorinating processes could provide an opportunity for environmental remediation, but detailed catalytic mechanisms for these enzymes are not yet known. To close this gap, we now report transient kinetics and product analysis of the dechlorinating flavin-dependent monooxygenase, HadA, from the aerobic organism Ralstonia pickettii DTP0602, identifying several mechanistic properties that differ from other enzymes in the same class. We first overexpressed and purified HadA to homogeneity. Analyses of the products from single and multiple turnover reactions demonstrated that HadA prefers 4-CP and 2-CP over CPs with multiple substituents. Stopped-flow and rapid-quench flow experiments of HadA with 4-CP show the involvement of specific intermediates (C4a-hydroperoxy-FAD and C4a-hydroxy-FAD) in the reaction, define rate constants and the order of substrate binding, and demonstrate that the hydroxylation step occurs prior to chloride elimination. The data also identify the non-productive and productive paths of the HadA reactions and demonstrate that product formation is the rate-limiting step. This is the first elucidation of the kinetic mechanism of a two-component flavin-dependent monooxygenase that can catalyze oxidative dechlorination of various CPs, and as such it will serve as the basis for future investigation of enzyme variants that will be useful for applications in detoxifying chemicals hazardous to human health.

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mentioning

confidence: 99%

Kinetic Mechanism of the Dechlorinating Flavin-dependent Monooxygenase HadA

Pimviriyakul

Thotsaporn

Sucharitakul

et al. 2017

Journal of Biological Chemistry

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“…Subordinate peaks observed at m/z 149, m/z 121, m/z 76 and m/z 73 in mass-spectra corresponding to different retention times were of L-methionine, alpha-methylbenzylamine, glycolic acid and isobutylamine respectively. Arora and Bae [47] reported that the anaerobic bacterial treatment of 2,4-dichloro phenol and 2-chloro phenol resulted in the formation of 4-hydroxybenzoic acid as an intermediate in different reaction pathways. In our earlier work [25], 4-hydroxybenzoic acid, D-glucuronic acid, maleic acid/fumaric acid and L-alanine has been identified as the major intermediates during the degradation of 4C2AP using the combined treatment of hydrodynamic cavitation, UV photolysis and ozone.…”

Section: Identification Of Intermediatesmentioning

confidence: 99%

Degradation of 4-chloro 2-aminophenol using combined approaches based on microwave and photocatalysis

Barik

Kulkarni

Gogate

2016

Separation and Purification Technology

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“…Complete mineralization of PCP and other CPs is possible through biodegradation, which is an effective and economic technique to remove these pollutants. PCP is more recalcitrant to bacterial degradation than less chlorinated CPs due to the presence of five chlorine atoms on the phenolic ring [17]. However, several strains of bacteria and fungi have been described in the literature as being able to degrade PCP aerobically or anaerobically.…”

Section: Toxicity and Bacterial Degradation Of Pcpmentioning

confidence: 99%

“…PcpE further converts 2-chloromaleylacetate into 3-oxoadipate via maleylacetate. Finally, 2-chloromaleylacetate is degraded in the tricarboxylic acid (TCA) cycle [17]. …”

Section: Toxicity and Bacterial Degradation Of Pcpmentioning

confidence: 99%

Bacterial Biotransformation of Pentachlorophenol and Micropollutants Formed during Its Production Process

Lopez-Echartea

Macek

Demnerova

et al. 2016

IJERPH

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Pentachlorophenol (PCP) is a toxic and persistent wood and cellulose preservative extensively used in the past decades. The production process of PCP generates polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans (PCDD/Fs) as micropollutants. PCDD/Fs are also known to be very persistent and dangerous for human health and ecosystem functioning. Several physico-chemical and biological technologies have been used to remove PCP and PCDD/Fs from the environment. Bacterial degradation appears to be a cost-effective way of removing these contaminants from soil while causing little impact on the environment. Several bacteria that cometabolize or use these pollutants as their sole source of carbon have been isolated and characterized. This review summarizes current knowledge on the metabolic pathways of bacterial degradation of PCP and PCDD/Fs. PCP can be successfully degraded aerobically or anaerobically by bacteria. Highly chlorinated PCDD/Fs are more likely to be reductively dechlorinated, while less chlorinated PCDD/Fs are more prone to aerobic degradation. The biochemical and genetic basis of these pollutants' degradation is also described. There are several documented studies of effective applications of bioremediation techniques for the removal of PCP and PCDD/Fs from soil and sediments. These findings suggest that biodegradation can occur and be applied to treat these contaminants.

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Bacterial degradation of chlorophenols and their derivatives

Cited by 187 publications

References 133 publications

Kinetic Mechanism of the Dechlorinating Flavin-dependent Monooxygenase HadA

Kinetic Mechanism of the Dechlorinating Flavin-dependent Monooxygenase HadA

Degradation of 4-chloro 2-aminophenol using combined approaches based on microwave and photocatalysis

Bacterial Biotransformation of Pentachlorophenol and Micropollutants Formed during Its Production Process

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