Format

Send to

Choose Destination
Biodegradation. 2018 Jun;29(3):259-270. doi: 10.1007/s10532-018-9827-z. Epub 2018 Mar 30.

Biodegradation of pentafluorosulfanyl-substituted aminophenol in Pseudomonas spp.

Author information

1
School of Biomolecular and Biomedical Science, University College Dublin, Belfield, Dublin 4, Ireland.
2
Dept of Environmental Science & Engineering, Government College University, Faisalabad, Pakistan.
3
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic.
4
Max F. Perutz Laboratories, University of Vienna, Vienna, Austria.
5
School of Biomolecular and Biomedical Science, University College Dublin, Belfield, Dublin 4, Ireland. Cormac.d.murphy@ucd.ie.

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

PMID:
29603052
DOI:
10.1007/s10532-018-9827-z
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for Springer
Loading ...
Support Center