Please use this identifier to cite or link to this item: http://dx.doi.org/10.18419/opus-8020
Authors: Engesser, Karl-Heinrich
Rubio, Miguel Angel
Ribbons, Douglas W.
Title: Bacterial metabolism of side chain fluorinated aromatics: cometabolism of 4-trifluoromethyl(TFM)-benzoate by 4-isopropylbenzoate grown Pseudomonas putida JT strains
Issue Date: 1988
metadata.ubs.publikation.typ: Zeitschriftenartikel
metadata.ubs.publikation.source: Archives of microbiology 149 (1988), S. 198-206. URL http://dx.doi.org./10.1007/BF00422005
URI: http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-76535
http://elib.uni-stuttgart.de/handle/11682/8037
http://dx.doi.org/10.18419/opus-8020
Abstract: Enzymes of the p-cymene pathway in Pseudomonas putida strains cometabolized the intermediate analogue 4-trifluoromethyl(TFM)benzoate. Three products, 4-TFM-2,3-dihydro-2,3-dihydroxybenzoate, 4-TFM-2,3-dihydroxy-benzoate and 2-hydroxy-6-oxo-7,7,7-trifluorohepta-2,4-dienoate (7-TFHOD) were identified chemically and by spectroscopic proterties.Certain TFM-substituted analogue metabolites of the p-cymene pathway were transformed at drastically reduced rates. Hammett type analysis of ring cleavage reactions of 4-substituted 2,3-dihydroxybenzoates revealed the negative inductive and especially mesomeric effect of substituents to be rate determining. Whereas decarboxylation of 3-carboxy-7-TFHOD was not affected by fluorine substitution the subsequent hydrolysis of 7-TFHOD proceeded very slowly. The negative inductive effect of the TFM-group probably inhibited heterolysis of the carbon bond between C5 and C6 of 7-TFHOD.
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