Mechanisms of bacterial degradation and transformation of chlorinated monoaromatic compounds

Abstract

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.