Biodegradation of pentafluorosulfanyl-substituted aminophenol in Pseudomonas spp.

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Title: Biodegradation of pentafluorosulfanyl-substituted aminophenol in Pseudomonas spp.
Authors: Saccomanno, MartaHussain, SabirO'Connor, Neil K.Murphy, Cormac al.
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Date: 1-Jun-2018
Online since: 2019-07-01T13:51:56Z
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.
Funding Details: European Commission - Seventh Framework Programme (FP7)
Irish Research Council
Type of material: Journal Article
Publisher: Springer Nature
Journal: Biodegradation
Volume: 29
Issue: 3
Start page: 259
End page: 270
Copyright (published version): 2018 Springer
Keywords: PseudomonasFluoridePentafluorosulfanylAminophenolsCatecholsMagnetic Resonance SpectroscopyBiotransformationBiodegradationMetabolomeEmerging pollutant
DOI: 10.1007/s10532-018-9827-z
Language: en
Status of Item: Peer reviewed
Appears in Collections:Biomolecular and Biomedical Science Research Collection

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