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

J Bacteriol. 1987 Nov;169(11):5125-30. doi: 10.1128/jb.169.11.5125-5130.1987.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aerobiosis
  • Anaerobiosis
  • Biotransformation
  • Chlorophenols / pharmacology*
  • Hydroquinones / metabolism*
  • Kinetics
  • Mass Spectrometry
  • Pentachlorophenol / pharmacology*
  • Rhodococcus / drug effects
  • Rhodococcus / metabolism*

Substances

  • Chlorophenols
  • Hydroquinones
  • 2,3,5,6-tetrachlorohydroquinone
  • Pentachlorophenol