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  • Title: Anaerobic transformation of phenol to benzoate via para-carboxylation: use of fluorinated analogues to elucidate the mechanism of transformation.
    Author: Genthner BR, Townsend GT, Chapman PJ.
    Journal: Biochem Biophys Res Commun; 1989 Aug 15; 162(3):945-51. PubMed ID: 2764948.
    Abstract:
    Isomeric fluorophenols were used as phenol analogues to investigate the transformation of phenol to benzoate by an anaerobic, phenol-degrading consortium derived from freshwater sediment. Transformation of 2-fluorophenol and 3-fluorophenol led to the accumulation of fluorobenzoic acids. 2-Fluorophenol was transformed in the presence or absence of phenol, while 3-fluorophenol transformation was only observed in the presence of phenol. Identification of the resulting fluorobenzoate products as 3-fluorobenzoate and 2-fluorobenzoate isomers, respectively, together with the nontransformation of 4-fluorophenol indicated that the carboxyl group was introduced para to the phenolic hydroxyl group.
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