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Reinscheid, Uwe M.; Zuilhof, Han; Müller, Rudolf; Vervoort, Jacques

doi:10.1023/a:1008394115008

Cited by 10 publications

(4 citation statements)

References 45 publications

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“…8 Proposed mechanism for the chemical decay of 3-(trifluoromethyl)catechol at 30°C and pH 7.5 (Engesser 1982). An analogous mechanism may be assumed for the chemical hydrolysis of 2-(trifluoromethyl)phenol at 60°C and pH 7.2 observed by Reinscheid et al (1998) defluorination was reported by these authors as well; however, only 2.5 % of the total fluorine supplied were recovered as fluoride.…”

Section: Side Chain Fluorinated Aromaticssupporting

confidence: 66%

“…T-12 produced 3-(trifluoromethyl)catechol from benzotrifluoride (Renganathan and Johnston 1989) and, as the m ain ca tec holic metabolite , from 3-fluorobenzotrifluoride (Renganathan 1989). 7-TFHOD accumulated in benzoate-grown cells of the bacterial strain V-1 during conversion of 3-(trifluoromethyl)benzoate (Taylor 1993) and during transformation of 2-(trifluoromethyl)phenol by thermophilic B. thermoleovorans A2 resting cells grown with LB (Reinscheid et al 1998). Temperature dependent chemical hydrolysis of 2-and 4-(trifluoromethyl)phenol under release of fluoride was observed by the latter authors.…”

Section: Side Chain Fluorinated Aromaticsmentioning

confidence: 76%

“…It was, however, reported to be hydrolyzed by sunlight (Taylor 1993;Reinscheid et al 1998). Findings regarding a release of fluoride ion during photolysis were inconsistent among these two work groups.…”

Section: Side Chain Fluorinated Aromaticsmentioning

confidence: 99%

“…The 2-hydroxy-6-oxo-hepta-2,4-dienoic acid hydrolases of numerous bacterial strains turned out to be unable to hydrolyze 7-TFHOD, suggesting this intermediate to be a general dead-end metabolite during metabolism of trifluoromethyl substituted compounds via meta cleavage pathways (Engesser et al 1988a(Engesser et al , b, 1990bTaylor 1993;Reinscheid et al 1998). It was, however, reported to be hydrolyzed by sunlight (Taylor 1993;Reinscheid et al 1998).…”

Section: Side Chain Fluorinated Aromaticsmentioning

confidence: 99%

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The biodegradation vs. biotransformation of fluorosubstituted aromatics

Kiel

Engesser

2015

Appl Microbiol Biotechnol

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Fluoroaromatics are widely and--in recent years--increasingly used as agrochemicals, starting materials for chemical syntheses and especially pharmaceuticals. This originates from the special properties the carbon-fluorine bond is imposing on organic molecules. Hence, fluoro-substituted compounds more and more are considered to be important potential environmental contaminants. On the other hand, the microbial potentials for their transformation and mineralization have received less attention in comparison to other haloaromatics. Due to the high electronegativity of the fluorine atom, its small size, and the extraordinary strength of the C-F bond, enzymes and mechanisms known to facilitate the degradation of chloro- or bromoarenes are not necessarily equally active with fluoroaromatics. Here, we review the literature on the microbial degradation of ring and side-chain fluorinated aromatic compounds under aerobic and anaerobic conditions, with particular emphasis being placed on the mechanisms of defluorination reactions.

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Section: Side Chain Fluorinated Aromaticssupporting

confidence: 66%