Anaerobic
Microbial Transformation of Halogenated
Aromatics and Fate Prediction Using Electron Density Modeling
Posted on 2015-05-19 - 00:00
Halogenated
homo- and heterocyclic aromatics including disinfectants,
pesticides and pharmaceuticals raise concern as persistent and toxic
contaminants with often unknown fate. Remediation strategies and natural
attenuation in anaerobic environments often build on microbial reductive
dehalogenation. Here we describe the transformation of halogenated
anilines, benzonitriles, phenols, methoxylated, or hydroxylated benzoic
acids, pyridines, thiophenes, furoic acids, and benzenes by Dehalococcoides mccartyi strain CBDB1 and environmental
fate modeling of the dehalogenation pathways. The compounds were chosen
based on structural considerations to investigate the influence of
functional groups present in a multitude of commercially used halogenated
aromatics. Experimentally obtained growth yields were 0.1 to 5 ×
1014 cells mol–1 of halogen released
(corresponding to 0.3–15.3 g protein mol–1 halogen), and specific enzyme activities ranged from 4.5 to 87.4
nkat mg–1 protein. Chlorinated electron-poor pyridines
were not dechlorinated in contrast to electron-rich thiophenes. Three
different partial charge models demonstrated that the regioselective
removal of halogens is governed by the least negative partial charge
of the halogen. Microbial reaction pathways combined with computational
chemistry and pertinent literature findings on CoI chemistry
suggest that halide expulsion during reductive dehalogenation is initiated
through single electron transfer from B12CoI to the apical halogen site.
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Cooper, Myriel; Wagner, Anke; Wondrousch, Dominik; Sonntag, Frank; Sonnabend, Andrei; Brehm, Martin; et al. (2016). Anaerobic
Microbial Transformation of Halogenated
Aromatics and Fate Prediction Using Electron Density Modeling. ACS Publications. Collection. https://doi.org/10.1021/acs.est.5b00303
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AUTHORS (8)
MC
Myriel Cooper
AW
Anke Wagner
DW
Dominik Wondrousch
FS
Frank Sonntag
AS
Andrei Sonnabend
MB
Martin Brehm
GS
Gerrit Schüürmann
LA
Lorenz Adrian