Anaerobic transformation of phenol to benzoate via para-carboxylation: use of fluorinated analogues to elucidate the mechanism of transformation.
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.
Genthner
B R
BR
Technical Resources, Inc, Gulf Breeze, FL.
Townsend
G T
GT
Chapman
P J
PJ
D000693:Anaerobiosis; D001565:Benzoates / Q000378:metabolism*; D019817:Benzoic Acid; D001711:Biotransformation; D006845:Hydrocarbons, Fluorinated; D013058:Mass Spectrometry; D019800:Phenol; D010636:Phenols / Q000378:metabolism*; D012722:Sewage; D014871:Water Microbiology / Q000379:methods*
D001565:Benzoates; D006845:Hydrocarbons, Fluorinated; D010636:Phenols; D012722:Sewage; D019800:Phenol; D019817:Benzoic Acid