Metabolism of fluoroorganic compounds in microorganisms: impacts for the environment and the production of fine chemicals

Murphy, Cormac D.; Clark, Benjamin R.; Amadio, Jessica

doi:10.1007/s00253-009-2127-0

Cited by 55 publications

(35 citation statements)

References 120 publications

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“…In the latter two cases, new peaks were also observed in the mass spectrum, at m/z 402/404, and 342, respectively, suggesting successful production of the target polyenes. Pyrrole-carboxylates with 40 larger substituents in the 4-position, 10-12, were not accepted as the biosynthetic starter unit, nor were the 5-substituted (13, 14) or di-substituted (15)(16)(17) acids. Supplementing the growth medium with pyrrole-2-carboxylic acid (6) led to an increased production of non-halogenated polyenes such as dechlororumbrin (2), as 45 reported previously.…”

Section: Resultsmentioning

confidence: 99%

“…Precursor-directed biosynthesis is a convenient way to introduce new atoms or groups into known natural products, in particular 30 halogens, which can impact on the biological activity of the compound in question 16 or provide a functionalizable handle for further modification. 17 These findings are of great interest as they show that the 3-chloropyrrole moiety is not absolutely essential for biological activity in this class of polyenes.…”

Section: Discussionmentioning

confidence: 99%

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Production of anticancer polyenes through precursor-directed biosynthesis

et al. 2011

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The biosynthesis of the pyrrolyl moiety of the fungal metabolite rumbrin originates from pyrrole-2-carboxylic acid. In an effort to produce novel derivatives with enhanced biological activity a series of substituted pyrrole-2-carboxylates were synthesised and incubated with the producing organism, Auxarthron umbrinum. Several 4-halo-pyrrole-2-carboxylic acids were incorporated into the metabolite yielding three new derivatives: 3-fluoro-, 3-chloro-and 3-bromo-isorumbrin, which were generated in 10 milligram quantities enabling cytotoxicity assays to be conducted. The 3-chloro-and 3-bromoisorumbrins had improved activity against HeLa cells compared with rumbrin; 3-bromoisorumbrin also showed dramatically improved activity towards a lung cancer cell line (A549).

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Production of anticancer polyenes through precursor-directed biosynthesis

et al. 2011

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“…The utility of aerobic granu l a r s l u d ge i n SB R f o r d eg r a d at i on of t o x i c organofluorine compounds such as 2-fluorophenol (2-FP) has been demonstrated [107]. The fluoroaromatic compounds are usually biodegraded via halo-catechols [108,109]. The maintenance of a good population of halo-aromatics degraders in bioreactors is highly desirable due to the low concentration discontinuous nature of these compounds [107].…”

Section: Recent Developments In the Application Of Sbrmentioning

confidence: 99%

Sequencing Batch Reactor for Wastewater Treatment: Recent Advances

2015

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Sequencing batch reactors (SBRs), due to its operational flexibility and excellent process control possibilities, are being extensively used for the treatment of wastewater which nowadays is fast becoming contaminated with newer and more complex pollutants. It is also possible to include different expanding array of configurations and various operational modifications to meet the effluent limits which are also continuously getting upgraded. This article provides basic description of SBR process along with its functional and physical variants that lead to improved the removal of nutrients and emerging contaminants. The significance of selectors and various recent advancements in the application of SBR has been discussed along with the possibilities held by SBR process in the treatment of wastewater of different origins and composition to produce effluent of reusable quality.

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“…The biodegradation of many chlorinated organic compounds has been studied (Chaudhry and Chapalamadugu 1991;Fetzner 1998;Haggblom 1992;Janssen et al 1994;van Pée and Unversucht 2003). The behavior of fluorinated compounds, such as fluorophenols and fluorobenzenes, has been less investigated (Key et al 1997;Murphy et al 2009;Murphy 2010), even though their use in agricultural and industrial processes is large, and cases of environmental contamination are becoming more frequent.…”

Section: Introductionmentioning

confidence: 98%

Isolation and characterization of a Rhodococcus strain able to degrade 2-fluorophenol

Duque

Hasan

Bessa

et al. 2011

Appl Microbiol Biotechnol

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A pure bacterial culture able to utilize 2-fluorophenol (2-FP) as sole carbon and energy source was isolated by selective enrichment from sediments collected from a contaminated site in Northern Portugal. 16S rRNA gene analysis showed that the organism (strain FP1) belongs to the genus Rhodococcus. When grown aerobically on 2-FP, growth kinetics of strain FP1 followed the Luong model. An inhibitory effect of increasing 2-FP concentrations was observed with no growth occurring at 2-FP levels higher than ca. 4 mM. Rhodococcus strain FP1 was able to degrade a range of other organofluorine compounds, including 2-fluorobenzoate, 3-fluorobenzoate, 4-fluorobenzoate, 3-fluorophenol, 4-fluorophenol, 3-fluorocatechol, and 4-fluorocatechol, as well as chlorinated compounds such as 2-chlorophenol and 4-chlorophenol. Experiments with cell-free extracts and partially purified enzymes indicated that the first step of 2-fluorophenol metabolism was conversion to 3-fluorocatechol, suggesting an unusual pathway for fluoroaromatic metabolism. To our knowledge, this is the first time that utilization of 2-FP as a growth substrate by a pure bacterial culture is reported.

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Metabolism of fluoroorganic compounds in microorganisms: impacts for the environment and the production of fine chemicals

Cited by 55 publications

References 120 publications

Production of anticancer polyenes through precursor-directed biosynthesis

Production of anticancer polyenes through precursor-directed biosynthesis

Sequencing Batch Reactor for Wastewater Treatment: Recent Advances

Isolation and characterization of a Rhodococcus strain able to degrade 2-fluorophenol

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