Bacterial methylation of chlorinated phenols and guaiacols: formation of veratroles from guaiacols and high-molecular-weight chlorinated lignin.

Two strains of bacteria, provisionally assigned to the genus Arthrobacter, were shown to metabolize mono-, di-, tri-, and tetrachloroguaiacols and pentachlorophenol to the corresponding O-methyl compounds. Hydroxylated intermediates were formed only transiently, except for the synthesis by one strain of 3,4,5-trichlorosyringol from 3,4,5-trichloroguaiacol. Two isomeric trichloroveratroles and tetrachloroveratrole were formed by three of the strains from a high-molecular-weight chlorinated lignin isolated from kraft pulp mill bleach plant. The concentrations of methylated metabolites varied widely and did not appear to be correlated with degradation. The possible environmental consequences resulting from synthesis of these highly lipophilic substances are discussed briefly.