Publication Details

Category Text Publication
Reference Category Journals
DOI 10.1021/acs.est.5b00303
Title (Primary) Anaerobic microbial transformation of halogenated aromatics and fate prediction using electron density modeling
Author Cooper, M.; Wagner, A.; Wondrousch, D.; Sonntag, F.; Sonnabend, A.; Brehm, M.; Schüürmann, G.; Adrian, L.
Source Titel Environmental Science & Technology
Year 2015
Department ISOBIO; OEC
Volume 49
Issue 10
Page From 6018
Page To 6028
Language englisch
UFZ wide themes RU3;
Abstract 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.
Persistent UFZ Identifier
Cooper, M., Wagner, A., Wondrousch, D., Sonntag, F., Sonnabend, A., Brehm, M., Schüürmann, G., Adrian, L. (2015):
Anaerobic microbial transformation of halogenated aromatics and fate prediction using electron density modeling
Environ. Sci. Technol. 49 (10), 6018 - 6028 10.1021/acs.est.5b00303