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NEW METABOLITES FROM THE MICROBIAL OXIDATION OF FLUORINATED AROMATIC COMPOUNDS. (R826113)

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Citation:

Hudlicky, T., D. Gonzalez, M. R. Stabile, M. A. Endoma, M. Deluca, D. Parker, D. T. Gibson, S. M. Resnick, AND G. M. Whited. NEW METABOLITES FROM THE MICROBIAL OXIDATION OF FLUORINATED AROMATIC COMPOUNDS. (R826113). ENVIRONMENTAL AND MOLECULAR MUTAGENESIS. American Chemical Society, Washington, DC, 89(1):23-30, (1998).

Description:

Abstract

m-Bromo-small alpha, Greek,small alpha, Greek,small alpha, Greek-trifluorotoluene (1) and 1-bromo-2,3-difluorobenzene (4) were subjected to microbial oxidation by Pseudomonas putida strain 39/D and the corresponding Escherichia coli recombinant microorganism (strain JM109(pDTG601)), which express toluene dioxygenase. The absolute stereochemistry of the major oxidation products have been determined as cis-(2R,3S)-5-bromo-2,3-dihydroxy-small alpha, Greek,small alpha, Greek,small alpha, Greek-trifluoromethylcyclohexa-4,6-diene (2), and cis-(2S,3S)-1-bromo-5,6-difluoro-2,3-dihydroxy-4,6-diene (5). The regiochemistry of a minor metabolite has been established as cis-5-bromo-3,4-dihydroxy-small alpha, Greek,small alpha, Greek,small alpha, Greek-trifluoromethylcyclohexa-1,5-diene (3).

Author Keywords: Toluene dioxygenase; Biooxidation; Microbial aromatic dihydroxylation; Fluorinated metabolites

Record Details:

Record Type:DOCUMENT( JOURNAL/ PEER REVIEWED JOURNAL)
Product Published Date:04/01/1998
Record Last Revised:12/22/2005
Record ID: 69177