Microbial dehalogenation

Janssen, Dick B.; Oppentocht, Jantien E.; Poelarends, Gerrit J.

doi:10.1016/s0958-1669(00)00208-1

Cited by 162 publications

(114 citation statements)

References 24 publications

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“…Various microbial dehalogenation reactions are known (Janssen et al, 2001). As discussed above, only one isomer of MBP-Br 6 Cl was detected in the samples examined.…”

Section: Origin and Distributionmentioning

confidence: 99%

Identification of highly brominated analogues of Q1 in marine mammals

Teuten

Pedler

Hangsterfer

et al. 2006

Environmental Pollution

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Capsule:Three compounds bioaccumulated in marine mammals were identified as C 9 H 3 N 2 Br 6 Cl, C 9 H 3 N 2 Br 7 and C 9 H 4 N 2 Br 5 Cl and are proposed to be 1'-methyl-1,2'-bipyrrole natural products.Keywords: bioaccumulation, halogenated organic compound, high resolution mass spectrometry, halogenated bipyrrole.* Corresponding author phone: +1 (508) 289-2641; fax: +1 (508) 457-2146; email: eteuten@whoi.edu. 1 AbstractThree novel halogenated organic compounds (HOCs) have been identified in the blubber of marine mammals from coastal New England with the molecular formulae C 9 H 3 N 2 Br 6 Cl, C 9 H 3 N 2 Br 7 , and C 9 H 4 N 2 Br 5 Cl. They were identified using high and low resolution electron ionization (EI) and electron capture negative ionization (ECNI) gas chromatography mass spectrometry (GCMS) and appear to be highly brominated analogues of Q1, a heptachlorinated HOC that has been suspected to be naturally-produced. These new compounds were found in Atlantic white sided dolphin (Lagenorhynchus acutus), bottlenose dolphin (Tursiops truncatus), common dolphin (Delphinus delphis), Risso's dolphin (Grampus griseus), harbor porpoise (Phocoena phocoena), beluga whale (Delphinapterus leucas), fin whale (Balaenoptera physalus), grey seal (Halichoerus grypus), harp seal (Phoca groenlandica) and a potential food source (Loligo pealei) with concentrations as high as 2.7 μg/g (lipid weight). The regiospecificity of C 9 H 3 N 2 Br 6 Cl is suggestive of a biogenic origin. Debromination of C 9 H 3 N 2 Br 6 Cl may be significant in the formation of C 9 H 4 N 2 Br 5 Cl.

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“…Various microbial dehalogenation reactions are known (Janssen et al, 2001). As discussed above, only one isomer of MBP-Br 6 Cl was detected in the samples examined.…”

Section: Origin and Distributionmentioning

confidence: 99%

Identification of highly brominated analogues of Q1 in marine mammals

Teuten

Pedler

Hangsterfer

et al. 2006

Environmental Pollution

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“…The halogen group serves as a significant barrier in metabolizing these compounds, and anaerobic bacteria are considered more efficient than aerobes in removing the halogen atoms from the polychlorinated biphenyls (2). Several reviews on the microbiology and enzymology of dehalogenation are available (2)(3)(4)(5)(6).…”

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confidence: 99%

Regulation of Anaerobic Dehalorespiration by the Transcriptional Activator CprK

Pop

Kolarik

Ragsdale

2004

Journal of Biological Chemistry

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Desulfomonile, Desulfitobacterium, and Dehalobacter are anaerobic microbes that can derive energy from the reductive dehalogenation of chlorinated organic compounds, many of which are environmental pollutants. There is very little information about how anaerobic dehalorespiration is regulated. An open reading frame within the Desulfitobacterium dehalogenans chlorophenol reductase (cpr) gene cluster (cprK) was proposed to be a transcriptional regulatory protein (Smidt, H., van Leest, M., van der Oost, J., and deVos, W. M. (2000) J. Bacteriol. 182, 5683-5691). We have cloned, actively overexpressed in Escherichia coli, and purified to homogeneity the D. dehalogenans CprK. The results of electrophoretic mobility shift assays, DNA footprinting studies, and promoter-lac fusion experiments indicate that CprK is a transcriptional activator of the cpr gene cluster. CprK binds 3-chloro-4-hydroxyphenylacetate (CHPA) with high affinity (K d ‫؍‬ 3.5 M, determined by isothermal titration calorimetry), which promotes its specific interaction with a DNA sequence (TTAAT-N4-ACTAA) located upstream of the ؊35 and ؊10 promoter regions of several cpr genes and activates transcription of these genes. Binding to the upstream "box" sequence increases the affinity of CprK for CHPA by ϳ10-fold (K d ‫؍‬ 0.4 M, determined by electrophoretic mobility shift assays). Chlorophenylacetate, which lacks the ortho-hydroxy group, and hydroxyphenylacetate, lacking the chlorine group, do not activate transcription or promote DNA binding, even at millimolar concentrations, at least 1000-fold higher than the K d value for CHPA. Lacking metals, CprK is oxygen-sensitive. Oxidation by diamide, which converts thiols to the disulfide, inactivates CprK, and reduction of the oxidized protein by dithiothreitol fully restores DNA binding, indicating that CprK is redox-regulated and is active only when reduced. This is the first reported characterization of a transcriptional regulator of anaerobic dehalorespiration.

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“…The persistence of these compounds in the environment causes considerable human health problems because of their toxicity and bioaccumulation in the food chain and ground water (Brokamp et al 1997;Dórea 2008). It is well-known that some organohalogen compounds degrade slowly and form toxic intermediates which may affect cellular metabolic processes (Slater et al 1995;Janssen et al 2001).…”

mentioning

confidence: 99%

Expression of haloacid dehalogenase gene and its molecular protein characterization from Klebsiella pneumoniae ITB1

Anggoro

Ratnaningsih

2018

Indones. J. Biotechnol.

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Organohalogen compounds are widely used industrially and agriculturally, as well as in households as flame retardants and refrigerants. However, these compounds can become significant pollutants through their accidental or deliberate release into the environment in large quan es. Dehalogenase is an enzyme with the poten al to be used in the removal of organohalogen contaminants. A previous study successfully subcloned a 690 bp of haloacid dehalogenase gene (hakp1) from Klebsiella pneumoniae ITB1 into a pET-30a(+) expression system to achieve high enzyme produc vity. IPTG was used as an inducer to express a pET-hakp1 recombinant clone in Escherichia coli BL21 (DE3). The molecular mass of the haloacid dehalogenase Hakp1 protein was 30 kDa as determined by SDS-PAGE. Zymogram analysis showed that this recombinant protein has dehalogenase ac vity as shown by the forma on of AgCl white precipitate. A quan ta ve assay of haloacid dehalogenase Hakp1 gave a specific ac vity of 84.29 U/mg with the op mum temperature of 40°C at pH 9. Predicted threedimensional structure of Hakp1 showed α/β mo f folding which comprised of cap and core domain. The predicted ac ve sites of Hakp1 were Asp8, Glu10, Leu22, Phe23, Trp90, Ser125, Ser126, Lys159, and Asp184 with Asp8, Glu10, Ser126, and Lys159 act as binding residue. This recombinant haloacid dehalogenase clone provides an alterna ve agent for effec ve bioremedia on of organohalogen pollutants.

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Microbial dehalogenation

Cited by 162 publications

References 24 publications

Identification of highly brominated analogues of Q1 in marine mammals

Identification of highly brominated analogues of Q1 in marine mammals

Regulation of Anaerobic Dehalorespiration by the Transcriptional Activator CprK

Expression of haloacid dehalogenase gene and its molecular protein characterization from Klebsiella pneumoniae ITB1

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