4-fluorocinnamic-acid and 4-fluorobenzoic-acid

Arthrobacter sp. strain G1 is able to grow on 4-fluorocinnamic acid (4-FCA) as sole carbon source. The organism converts 4-FCA into 4-fluorobenzoic acid (4-FBA) and utilizes the two-carbon side-chain for growth with some formation of 4-fluoroacetophenone as a dead-end side product. We also have isolated Ralstonia sp. strain H1, an organism that degrades 4-FBA. A consortium of strains G1 and H1 degraded 4-FCA with Monod kinetics during growth in batch and continuous cultures. Specific growth rates of strain G1 and specific degradation rates of 4-FCA were observed to follow substrate inhibition kinetics, which could be modeled using the kinetic models of Haldane-Andrew and Luong-Levenspiel. The mixed culture showed complete mineralization of 4-FCA with quantitative release of fluoride, both in batch and continuous cultures. Steady-state chemostat cultures that were exposed to shock loadings of substrate responded with rapid degradation and returned to steady-state in 10-15 h, indicating that the mixed culture provided a robust system for continuous 4-FCA degradation.

Topics: Arthrobacter; Batch Cell Culture Techniques; Benzoates; Biodegradation, Environmental; Biomass; Carbon; Cinnamates; Kinetics; Microbial Consortia; Ralstonia; Water Pollutants, Chemical

A consortium of the newly isolated bacterial strains Arthrobacter sp. strain G1 and Ralstonia sp. strain H1 utilized 4-fluorocinnamic acid for growth under aerobic conditions. Strain G1 converted 4-fluorocinnamic acid into 4-fluorobenzoic acid and used the two-carbon side chain for growth, with some formation of 4-fluoroacetophenone as a dead-end side product. In the presence of strain H1, complete mineralization of 4-fluorocinnamic acid and release of fluoride were obtained. Degradation of 4-fluorocinnamic acid by strain G1 occurred through a β-oxidation mechanism and started with the formation of 4-fluorocinnamoyl-coenzyme A (CoA), as indicated by the presence of 4-fluorocinnamoyl-CoA ligase. Enzymes for further transformation were detected in cell extract, i.e., 4-fluorocinnamoyl-CoA hydratase, 4-fluorophenyl-β-hydroxy propionyl-CoA dehydrogenase, and 4-fluorophenyl-β-keto propionyl-CoA thiolase. Degradation of 4-fluorobenzoic acid by strain H1 proceeded via 4-fluorocatechol, which was converted by an ortho-cleavage pathway.

Topics: Anaerobiosis; Arthrobacter; Benzoates; Biotransformation; Cinnamates; Cluster Analysis; DNA, Bacterial; DNA, Ribosomal; Fluorides; Metabolic Networks and Pathways; Molecular Sequence Data; Phylogeny; Ralstonia; RNA, Ribosomal, 16S; Sequence Analysis, DNA

The biotransformation of 4-fluorocinnamic acid (FCA) using non-acclimated industrial activated sludge was investigated. FCA is a common intermediate in organic synthesis, and it is often present in aqueous waste streams. Hence, the biotransformation reactions this compound undergoes when exposed to activated sludge micro-organisms should be understood before waste streams are sent to biological wastewater treatment plants (WWTPs). FCA biotransformation was monitored using a wide range of analytical techniques. These techniques were used to monitor not only FCA disappearance, but also the formation of degradation products, in order to propose the metabolic pathway. FCA was biotransformed to 4-fluorobenzoic acid via the formation of 4-fluoroacetophenone. The removal of FCA up to 200 mg L(-1) followed first order kinetics. The half-lives for removal of FCA from the test solutions supplied with 200 mg L(-1), 100 mg L(-1), and 50 mg L(-1) were 53, 18, and 5 hours respectively.

Topics: Aerobiosis; Benzoates; Biodegradation, Environmental; Biotransformation; Chromatography, High Pressure Liquid; Cinnamates; Gas Chromatography-Mass Spectrometry; Industrial Waste; Magnetic Resonance Spectroscopy; Models, Chemical; Sewage; Waste Disposal, Fluid; Water Pollutants, Chemical