The metabolism of p-fluorobenzoic acid by a Pseudomonas sp.

Abstract

1971. The metabolism ofp-fluorobenzoic acid by a Pselrdonionas sp. Can. J. Microbial. 17: 1015-1023.A species of Pselido~nonas previously used to study the degradation of p-fluorophenylacetic acid was used to investigate the degradation of p-fluorobenzoic acid. During growth on the latter substrate all organic fluorine was released into the culture medium as fluoride. Several metabolic intermediates were isolated from the culture medium of resting cells. The major compounds have been identified as 4-fluorocatechol, p-acetylacrylic acid, (+)-4-carboxymethyl-4-fluorobut-2-enolide, (-)-4-carboxymethylbut-2-enolide, and 0-ketoadipic acid. A small quantity of a compound tentatively identified as p-fluoroacrylic acid was also isolated. On the basis of these findings, together with respiratory studies on pfluorobenzoic acid grown cells with various substrates, two metabolic pathways are proposed which involve elimination of fluorine at either of two alternative stages in the breakdown ofp-fluorobenzoic acid.

Analysis of Two Gene Clusters Involved in the Degradation of 4-Fluorophenol by Arthrobacter sp. Strain IF1

“…Defluorination of fluoroaromatics can occur prior to ring cleavage, e.g., via an oxygenase that defluorinates fluorobenzoate (11,36) or fluorobenzene (8). In other cases, defluorination occurs after ring cleavage via the formation of fluorinated muconolactones (42), which can be produced from 4-fluorobenzoate (19) and fluorobenzene (8) via 4-fluorocatechol. Bacterial and fungal phenol hydroxylases can convert fluorophenols to fluorocatechols or fluoropyrogallols, which are metabolized to fluoromuconic acids by ring cleavage dioxygenases (5,6).…”

Isolation and Initial Characterization of a Bacterial Consortium Able To Mineralize Fluorobenzene

“…Although degradation under aerobic conditions is usually reported, anaerobic degradation of fluorobenzoates under denitrifying conditions has also been reported (26). The existence of various metabolic pathways, some of which may lead to the formation of inhibitor metabolites, has been reported (15,24,25). In some cases, as in the degradation of fluoroacetate, a specific enzyme is responsible for the cleavage of the C-F bond (12).…”

“…Examples of biodegradation of fluorinated compounds most commonly found in the literature involve fluorobenzoic acids (7,15,20,21,24) and fluorophenols (1, 2, 23). Although degradation under aerobic conditions is usually reported, anaerobic degradation of fluorobenzoates under denitrifying conditions has also been reported (26).…”

Complete Biodegradation of 4-Fluorocinnamic Acid by a Consortium Comprising Arthrobacter sp. Strain G1 and Ralstonia sp. Strain H1

“…Mineralization of 4-FBA and fluoride release were possible only when strain H1 was present in coculture with strain G1, since Arthrobacter G1 is not able to use 4-FBA as a growth substrate. Microbial cleavage of the aromatic ring of 4-FBA can occur before or after defluorination (3,10,17,33,43,45). In the first case, the initial step in 4-FBA degradation is the substitution of fluorine to yield 4-hydroxybenzoic acid, which occurs in Aureobacterium sp.…”

“…However, little information is available about the microbial metabolism of fluorinated organic compounds compared to other halogenated chemicals. Most studies on the bacterial degradation of fluorinated organics describe fluorobenzoic acids, which under aerobic conditions can be converted into the corresponding fluorocatechols (3,17,33). Papers about the degradation of fluorophenols have also appeared (11,25,51).…”