Oxidation of 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane (DDT) by Alcaligenes eutrophus A5

Arch Microbiol. 1998 Dec;171(1):44-9. doi: 10.1007/s002030050676.

Abstract

Previous studies demonstrated that Alcaligenes eutrophus A5 transforms 1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane (DDT) to 4-chlorobenzoate via a meta-ring fission product. The initial reactions could be catalyzed by either monooxygenase or dioxygenase enzymes. In the present study, a transient intermediate that accumulated during the transformation of DDT by the biphenyl-grown cells was identified as 1,1,1-trichloro-2-(4-chlorophenyl-2,3-dihydro-4,6-cyclohexadiene)-2-(4'- chlorophenyl)ethane (DDT-2,3-dihydrodiol) on the basis of mass spectral analysis after n-butylboronic acid derivatization. The dihydrodiol undergoes a characteristic acid-catalyzed dehydration to produce phenols. 1H-NMR indicated a cis-relative stereochemistry. The results indicate that the biphenyl dioxygenase from A. eutrophus A5 catalyzes the dihydroxylation of DDT at the unsubstituted carbons on the aromatic ring to produce DDT-2,3-dihydrodiol.

MeSH terms

  • Alcaligenes / metabolism*
  • Biodegradation, Environmental
  • Biphenyl Compounds / chemistry
  • Culture Media / chemistry
  • DDT / metabolism*
  • Insecticides / metabolism*
  • Mass Spectrometry
  • Oxidation-Reduction
  • Oxygenases / isolation & purification
  • Oxygenases / metabolism
  • Succinic Acid / chemistry
  • Toluene / chemistry

Substances

  • Biphenyl Compounds
  • Culture Media
  • Insecticides
  • diphenyl
  • Toluene
  • Succinic Acid
  • DDT
  • Oxygenases