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

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.

• Authors: L J Nadeau, G S Sayler, J C Spain
• Journal: Archives of microbiology (Arch Microbiol) Vol. 171 Issue 1 Pg. 44-9 (Dec 1998) ISSN: 0302-8933 [Print] Germany
• PMID: 9871018 (Publication Type: Journal Article)

Chemical References

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

Topics

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