Enzymatic binding of the pollutant 2,6-xylenol to a humus constituent

Dimeric and polymeric hybrid oliogmers were obtained by the reaction of 2,6-xylenol and syringic acid in the presence of an enzyme from the fungus Trametes versicolor. Three hybrid dimers were formed in an assay at pH 4.5, while at pH 6.5, the formation of additional higher polymers with a phenyl-ether bond (tail to head linkage) was detected. The major product was identified as 3,5-dimethyl-3′,5′-dimethoxydiphenoquinone (4,4′), and it amounted to approximately 45% of the applied 2,6-xylenol after 3.5 hr incubation at pH 4.5. About 8% of the 2,6-xylenol was transformed to 4,4′-dihydroxy-3,5-dimethyl-3′,5′-dimethoxydiphenol and 22% to 3-methoxy-5-(2′,6′-dimethylphenoxy)-benzoquinone (1,2).