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Microbial Synthesis and Transformation of Inorganic and Organic Chlorine Compounds

Atashgahi, Siavash, Liebensteiner, Martin G., Janssen, Dick B., Smidt, Hauke, Stams, Alfons J. M., Sipkema, Detmer·2018·Frontiers in Microbiology
DOI 10.3389/fmicb.2018.03079PMC PMC6299022
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FIGURE 1 Selected chlorine compounds, their origin and (bio)transformation – a schematic overview of the global chlorine cycle. Representative microbial dechlorination processes and involved compounds are shown in green boxes. The most abundant biologically produced chlorine compounds are indicated in orange, whereas examples for local “microcycles” are highlighted in blue. Groups of (micro)organisms associated with a particular metabolism are indicated in italics. Solid and dotted lines illustrate biological and chemical processes, respectively.
FIGURE 1 Selected chlorine compounds, their origin and (bio)transformation – a schematic overview of the global chlorine cycle. Representative microbial dechlorination processes and involved compounds are shown in green boxes. The most abundant biologically produced chlorine compounds are indicated in orange, whereas examples for local “microcycles” are highlighted in blue. Groups of (micro)organisms associated with a particular metabolism are indicated in italics. Solid and dotted lines illustrate biological and chemical processes, respectively.CC BY · PubMed Central
FIGURE 2 Schematic overview of enzymatic chlorination reactions. Reaction 1 is an electrophilic chlorination reaction of an alkyl group (R) catalyzed by heme- or vanadium-containing chloroperoxidases. Reactions 2 and 3 are nucleophilic chlorination reactions catalyzed by SAM-dependent methyl transferases that lead to the formation of mono substituted alkanes (2) or to the formation of 5′-chloro deoxyadenosine (3), which is the precursor of salinosporamide A. Reaction 4 is a radical chlorination at unactivated carbon centers and is catalyzed by an α-ketoglutarate-dependent non-heme iron chlorinase. Reaction 5 mainly leads to chlorination of tryptophan, phenol or pyrrole ring structures catalyzed by FADH2-dependent chlorinases. R1 represents a phenol, pyrrole or tryptophan moiety.
FIGURE 2 Schematic overview of enzymatic chlorination reactions. Reaction 1 is an electrophilic chlorination reaction of an alkyl group (R) catalyzed by heme- or vanadium-containing chloroperoxidases. Reactions 2 and 3 are nucleophilic chlorination reactions catalyzed by SAM-dependent methyl transferases that lead to the formation of mono substituted alkanes (2) or to the formation of 5′-chloro deoxyadenosine (3), which is the precursor of salinosporamide A. Reaction 4 is a radical chlorination at unactivated carbon centers and is catalyzed by an α-ketoglutarate-dependent non-heme iron chlorinase. Reaction 5 mainly leads to chlorination of tryptophan, phenol or pyrrole ring structures catalyzed by FADH2-dependent chlorinases. R1 represents a phenol, pyrrole or tryptophan moiety.CC BY · PubMed Central
FIGURE 3 Tree of life showing the phyla or classes for which key enzymes of microbial (de)chlorination processes have been detected. The tree of life was prepared from the Silva SSU Ref NR 115 database. The bar illustrates a distance of 0.1 substitutions per site. Organisms that carry aerobic haloalkane dehalogenases are indicated by a yellow square. Reductive dehalogenase-baring organisms are shown by the blue triangle, organisms with chlorate- and perchlorate-reducing enzymes by the green circle and halogenase-producing organisms by the red star.
FIGURE 3 Tree of life showing the phyla or classes for which key enzymes of microbial (de)chlorination processes have been detected. The tree of life was prepared from the Silva SSU Ref NR 115 database. The bar illustrates a distance of 0.1 substitutions per site. Organisms that carry aerobic haloalkane dehalogenases are indicated by a yellow square. Reductive dehalogenase-baring organisms are shown by the blue triangle, organisms with chlorate- and perchlorate-reducing enzymes by the green circle and halogenase-producing organisms by the red star.CC BY · PubMed Central
FIGURE 4 Productive routes for utilization of selected organochlorine compounds in bacteria. (A) Initial step in chlorothalonil degradation, catalyzed by a dehalogenase (CTD) (Liang et al., 2011). (B) 1,3-dichloropropene degradation by Pseudomonas pavonaceae (Poelarends et al., 1998). The initial dehalogenase (DhaA) is found in haloalkane-degrading bacteria from different geographic regions, whereas the second dehalogenase (CaaD) is unrelated and rare (Poelarends et al., 2000). (C) Pentachlorophenol metabolism by an initial monooxygenase (PcpB) reaction and two reductive reactions, the first one (PcpC) involving a glutathione transferase, and the second one (PcpE) involving an NADH-dependent reductase (Kiefer and Copley, 2002; Hlouchova et al., 2012). (D) Degradation of 2,3-dichloropropanol via the highly reactive intermediate 2-chloroacrolein (Arif et al., 2012). (E) The insecticide hexachlorohexane undergoes two initial dechlorinations by elimination by a dehalogenase (LinA). (F) Aerobic methylchloride metabolism involving a corrinoid cofactor of the methyltransferase (CmuA) and tetrahydrofolate (THF) as methyl acceptor (Stourman et al., 2003).
FIGURE 4 Productive routes for utilization of selected organochlorine compounds in bacteria. (A) Initial step in chlorothalonil degradation, catalyzed by a dehalogenase (CTD) (Liang et al., 2011). (B) 1,3-dichloropropene degradation by Pseudomonas pavonaceae (Poelarends et al., 1998). The initial dehalogenase (DhaA) is found in haloalkane-degrading bacteria from different geographic regions, whereas the second dehalogenase (CaaD) is unrelated and rare (Poelarends et al., 2000). (C) Pentachlorophenol metabolism by an initial monooxygenase (PcpB) reaction and two reductive reactions, the first one (PcpC) involving a glutathione transferase, and the second one (PcpE) involving an NADH-dependent reductase (Kiefer and Copley, 2002; Hlouchova et al., 2012). (D) Degradation of 2,3-dichloropropanol via the highly reactive intermediate 2-chloroacrolein (Arif et al., 2012). (E) The insecticide hexachlorohexane undergoes two initial dechlorinations by elimination by a dehalogenase (LinA). (F) Aerobic methylchloride metabolism involving a corrinoid cofactor of the methyltransferase (CmuA) and tetrahydrofolate (THF) as methyl acceptor (Stourman et al., 2003).CC BY · PubMed Central
FIGURE 5 Anaerobic dehalogenation mechanisms. Reductive dechlorination by (A) hydrogenolysis, (B) dihaloelimination.
FIGURE 5 Anaerobic dehalogenation mechanisms. Reductive dechlorination by (A) hydrogenolysis, (B) dihaloelimination.CC BY · PubMed Central
FIGURE 6 Microbial reduction of chlorine oxyanions – a schematic overview. (A) “classical” perchlorate reduction involving a functional chlorite dismutase (Cld, mainly found in mesophilic Proteobacteria), (B) reduction of chlorine oxyanions in the absence of Cld, employing an “intraspecies sulfur loop” (as found in A. fulgidus), (C) potential syntrophic reduction of chlorate and perchlorate, involving interspecies sulfur transfer. Perchlorate-reducing enzymes are depicted in green, chlorite dismutase in red and terminal oxidase in blue. Enzymes involved in the reduction of oxidized sulfur compounds (e.g., S0, S2O32-, S4O62-, etc.) are shown in yellow.
FIGURE 6 Microbial reduction of chlorine oxyanions – a schematic overview. (A) “classical” perchlorate reduction involving a functional chlorite dismutase (Cld, mainly found in mesophilic Proteobacteria), (B) reduction of chlorine oxyanions in the absence of Cld, employing an “intraspecies sulfur loop” (as found in A. fulgidus), (C) potential syntrophic reduction of chlorate and perchlorate, involving interspecies sulfur transfer. Perchlorate-reducing enzymes are depicted in green, chlorite dismutase in red and terminal oxidase in blue. Enzymes involved in the reduction of oxidized sulfur compounds (e.g., S0, S2O32-, S4O62-, etc.) are shown in yellow.CC BY · PubMed Central

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Metadata

Authors
Atashgahi, S., Liebensteiner, M. G., Janssen, D. B., Smidt, H., Stams, A. J. M., & Sipkema, D.
Venue
Frontiers in Microbiology
Publisher
Frontiers Media SA
Published
2018-12-12
Volume
9
ISSN
1664-302X
DOI
10.3389/fmicb.2018.03079
PMC
PMC6299022
Cited by
64
References
7
Licence
creativecommons.org/licenses/by/4.0/ (unspecified)
Funders
Wageningen University and Research Centre

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