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In this paper we describe the sequence of reactions leading from tetrachloro-para-hydroquinone to 1,2,4-trihydroxybenzene by inducible enzymes of Rhodococcus chlorophenolicus. Tetrachlorohydroquinone was first converted to a dichlorotrihydroxybenzene in a reaction involving both hydrolytic and reductive dechlorination; no trichlorinated intermediate was detected. Dichlorotrihydroxybenzene was subsequently reductively dechlorinated to a monochlorotrihydroxybenzene and finally to 1,2,4-trihydroxybenzene. The cell extract also catalyzed, at a lower rate, reductive dechlorination of trichlorohydroquinone, mainly to 2,3-dichlorohydroquinone. To our knowledge this is the first demonstration of reductive aromatic dechlorination by bacterial enzymes.

Complete dechlorination of tetrachlorohydroquinone by cell extracts of pentachlorophenol-induced Rhodococcus chlorophenolicus