Bacterial Methylation of Chlorinated Phenols and Guaiacols: Formation of Veratroles from Guaiacols and High-Molecular-Weight Chlorinated Lignin

Neilson, Alasdair H.; Allard, Ann‐Sofie; Hynning, Per‐Åke; Remberger, Mikael; Landner, Lars

doi:10.1128/aem.45.3.774-783.1983

Cited by 111 publications

(64 citation statements)

References 25 publications

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“…Several species of Gram-positive and Gramnegative bacteria belonging to the genera Acinetobacter, Pseudomonas, Mycobacterium, and Rhodococcus have been shown to O-methylate chlorinated phenols and chlorophenol derivatives [104,[106][107][108][109][110][111][112]. O-Methylation of chlorophenols to the corresponding chloroanisoles has also frequently been observed with different species of fungi [71,[113][114][115][116][117].…”

Section: Biotransformation Of Chlorinated Phenolic Compoundsmentioning

confidence: 99%

Microbial breakdown of halogenated aromatic pesticides and related compounds

Häggblom

1992

FEMS Microbiology Letters

363

132

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Considerable progress has been made in the last few years in understanding the mechanisms of microbial degradation of halogenated aromatic compounds. Much is already known about the degradation mechanisms under aerobic conditions, and metabolism under anaerobiosis has lately received increasing attention. The removal of the halogen substituent is a key step in degradation of halogenated aromatics. This may occur as an initial step via reductive, hydrolytic or oxygenolytic mechanisms, or after cleavage of the aromatic ring at a later stage of metabolism. In addition to degradation, several biotransformation reactions, such as methylation and polymerization, may take place and produce more toxic or recalcitrant metabolites. Studies with pure bacterial and fungal cultures have given detailed information on the biodegradation pathways of several halogenated aromatic compounds. Several of the key enzymes have been purified or studied in cell extracts, and there is an increasing understanding of the organization and regulation of the genes involved in haloaromatic degradation. This review will focus on the biodegradation and biotransformation pathways that have been established for halogenated phenols, phenoxyalkanoic acids, benzoic acids, benzenes, anilines and structurally related halogenated aromatic pesticides. There is a growing interest in developing microbiological methods for clean‐up of soil and water contaminated with halogenated aromatic compounds.

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Section: Biotransformation Of Chlorinated Phenolic Compoundsmentioning

confidence: 99%

Microbial breakdown of halogenated aromatic pesticides and related compounds

Häggblom

1992

FEMS Microbiology Letters

363

132

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“…Several species of bacteria belonging to the genera Acinetobacter, Pseudomonas, Rhodococcus, and Mycobacterium have been shown to 0-methylate chlorinated phenols and phenol derivatives (guaiacols, syringols, catechols, hydroquinones, phenoxy phenols) (ALLARD et al 1985, HAGCBLOM 1988, HAGCBLOM et al 1988b, d, 1989b, NEILSON et al 1983, SUZUKI 1978, VALQ and SALKINOJA-SALONEN 1986. Chloroveratroles were also formed by bacteria from high-molecular-weight chlorolignin, probably by 0-methylation of chloroguaiacols released from the chemically unstable chlorolignin (ERIKSSON et al 1985, NEILSON et al 1983).…”

Section: -Methylation Of Clorinated Phenolic Compoundsmentioning

confidence: 99%

“…Similar reaction sequences were observed in the transformation of 3,4,5-trichloroguaiacol by a Rhodococcus sp. (NEILSON et al 1983). These studies exemplify the transformation of chlorinated phenolic compounds involving several sequential reactions with no actual attack on the carbon skeleton.…”

Section: -Methylation Of Clorinated Phenolic Compoundsmentioning

confidence: 99%

Mechanisms of bacterial degradation and transformation of chlorinated monoaromatic compounds

Häggblom

1990

J. Basic Microbiol.

115

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Chloroaromatics are xenobiotic compounds of environmental concern. They can be removed from the environment by (bio)degradation or by (bio)transformation. Recognition of the mechanisms and requirements of their biodegradation is of cardinal importance for understanding the fate of these chemicals in the environment, and for developing methods for biological treatment of wastes containing compounds of this type. Cleavage of the carbon-halogen bond is the critical step in degradation of chloroaromatics. As exemplified with chlorophenols, chlorobenzoates and chlorobenzenes in this review, two distinct strategies are employed by bacteria for degradation of chlorinated aromatic compounds: the particular chlorine substituents are removed either directly from the aromatic ring (as an initial step in degradation) or after oxygenative ring cleavage (from chlorinated aliphatic intermediates). Direct elimination of chlorine substituents from the aromatic ring occurs by displacement with either hydroxyl groups (hydrolytically or oxygenolytically) or hydrogen atoms (reductive dechlorination). Dechlorinations of the latter type require reducing power and are significant in anaerobic environments, but have also been observed with strictly aerobic bacteria. Various biotransformation reactions, with only minor alteration of the parent compound, are an alternative to biogradation. Two environmentally significant transformation reactions discussed here are O-methylation and O-demethylation. The capability to O-methylate chlorinated hydroxybenzenes seems to be widespread in bacteria. O-Methylation is an environmentally important transformation reaction, since methylation increases the lipophilicity of the compound and thus the potential for bioaccumulation. Bacterial O-demethylation of chlorinated methoxylated compounds has been observed under both aerobic and anaerobic conditions.

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“…In addition, some phenolic compounds, for example 3.43-trichloroguaiacol ( Fig. 18) (Neilson et a/. 1983) and chlorophenols (Haggblom et a/.…”

Section: Biodegradation and Biotransformationmentioning

confidence: 99%