Biodegradation of pentafluorosulfanyl-substituted aminophenol in Pseudomonas spp.

  • Marta Saccomanno
  • Sabir Hussain
  • Neil K. O’Connor
  • Petr Beier
  • Mate Somlyay
  • Robert Konrat
  • Cormac D. Murphy
Original Paper

Abstract

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.

Keywords

Biodegradation Emerging pollutant Fluoride Pentafluorosulfanyl Pseudomonas 

Notes

Acknowledgements

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.

Supplementary material

10532_2018_9827_MOESM1_ESM.docx (147 kb)
Supplementary material 1 (DOCX 146 kb)

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© Springer Science+Business Media B.V., part of Springer Nature 2018

Authors and Affiliations

  1. 1.School of Biomolecular and Biomedical ScienceUniversity College DublinDublin 4Ireland
  2. 2.Institute of Organic Chemistry and BiochemistryAcademy of Sciences of the Czech RepublicPragueCzech Republic
  3. 3.Max F. Perutz LaboratoriesUniversity of ViennaViennaAustria
  4. 4.Dept of Environmental Science & EngineeringGovernment College UniversityFaisalabadPakistan

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