Biodegradation of pentafluorosulfanyl-substituted aminophenol in Pseudomonas spp.
- 230 Downloads
The pentafluorosulfanyl (SF5–) substituent conveys properties that are beneficial to drugs and agrochemicals. As synthetic methodologies improve the number of compounds containing this group will expand and these chemicals may be viewed as emerging pollutants. As many microorganisms can degrade aromatic xenobiotics, we investigated the catabolism of SF5-substituted aminophenols by bacteria and found that some Pseudomonas spp. can utilise these compounds as sole carbon and energy sources. GC–MS analysis of the culture supernatants from cultures grown in 5-(pentafluorosulfanyl) 2-aminophenol demonstrated the presence of the N-acetylated derivative of the starting substrate and 4-(pentafluorosulfanyl)catechol. Biotransformation experiments with re-suspended cells were also conducted and fluorine-19 NMR analyses of the organic extract and aqueous fraction from suspended cell experiments revealed new resonances of SF5-substituted intermediates. Supplementation of suspended cell cultures with yeast extract dramatically improved the degradation of the substrate as well as the release of fluoride ion. 4-(Pentafluorosulfanyl)catechol was shown to be a shunt metabolite and toxic to some of the bacteria. This is the first study to demonstrate that microorganisms can biodegrade SF5-substituted aromatic compounds releasing fluoride ion, and biotransform them generating a toxic metabolite.
KeywordsBiodegradation Emerging pollutant Fluoride Pentafluorosulfanyl Pseudomonas
This work was supported by the Initial Training Network, FLUOR21, funded by the FP7 Marie Curie Actions of the European Commission (FP7-PEOPLE-2013-ITN-607787). SH was supported by an Irish Research Council Government of Ireland Postdoctoral Fellowship.
- Davis KJ, He Z, Somerville CC, Spain CJ (1999) Genetic and biochemical comparison of 2-aminophenol 1,6-dioxygenase of Pseudomonas pseudoalcaligenes JS45 to meta-cleavage dioxygenases: divergent evolution of 2-aminophenol meta-cleavage pathway. Arch Microbiol 172(5):330–339. https://doi.org/10.1007/s002030050787 CrossRefPubMedGoogle Scholar
- Gaillard M, Vallaeys T, Vorholter FJ, Minoia M, Werlen C, Sentchilo V, Puhler A, van der Meer JR (2006) The clc element of Pseudomonas sp strain B13, a genomic island with various catabolic properties. J Bacteriol 188(5):1999–2013. https://doi.org/10.1128/jb.188.5.1999-2013.2006 CrossRefPubMedPubMedCentralGoogle Scholar
- Hendriks CMM, Penning TM, Zang TZ, Wiemuth D, Grunder S, Sanhueza IA, Schoenebeck F, Bolm C (2015) Pentafluorosulfanyl-containing flufenamic acid analogs: syntheses, properties and biological activities. Bioorg Med Chem Lett 25(20):4437–4440. https://doi.org/10.1016/j.bmcl.2015.09.012 CrossRefPubMedPubMedCentralGoogle Scholar