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  5. Microbial biotransformation of aryl sulfanylpentafluorides
 
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Microbial biotransformation of aryl sulfanylpentafluorides

Author(s)
Kavanagh, Emma  
Winn, Michael  
Nic Gabhann, Cliona  
O'Connor, Neil K.  
Beier, Petr  
Murphy, Cormac D.  
Uri
http://hdl.handle.net/10197/6342
Date Issued
2014-01
Date Available
2015-02-05T12:41:10Z
Abstract
We report, for the first time, the biotransformation of potential pollutants bearing the pentafluorosulfanyl (SF5-) functional group in a fungus and bacteria. Cunninghamella elegans transformed p-methoxy phenyl SF5 via demethylation; Pseudomonas knackmussii and P. pseudoalcaligenes KF707 transformed amino-, hydroxyamino- and diamino- substituted phenyl SF5, forming the N-acetylated derivatives as the main product. Cell-free extract of Streptomyces griseus transformed 4-amino-3-hydroxy-phenyl SF5 to the N-acetylated derivative in the presence of acetyl CoA, confirming that an N-acetyltransferase is responsible for the bacterial biotransformations. Approximately 25 % of drugs and 30 % of agrochemicals contain fluorine, and the trifluoromethyl group is a prominent feature of many of these since it improves lipophilicity and stability. The pentafluorosulfanyl substituent is seen as an improvement on the trifluoromethyl group and research efforts are underway to develop synthetic methods to incorporate this moiety into biologically active compounds. It is important to determine the potential environmental impact of these compounds, including the potential biotransformation reactions that may occur when they are exposed to microorganisms.
Sponsorship
Irish Research Council
Science Foundation Ireland
Other Sponsorship
Society for General Microbiology (UK)
Grant Agency of the Czech Republic
Academy of Sciences of the Czech Republic
Type of Material
Journal Article
Publisher
Springer
Journal
Environmental Science and Pollution Research
Volume
21
Issue
1
Start Page
753
End Page
758
Copyright (Published Version)
2013 Springer
Subjects

Fluorine

Emerging pollutant

N-acetylation

DOI
10.1007/s11356-013-1985-2
Language
English
Status of Item
Peer reviewed
This item is made available under a Creative Commons License
https://creativecommons.org/licenses/by-nc-nd/3.0/ie/
File(s)
No Thumbnail Available
Name

Biotransformation_of_PhSF5_ESPR_Revision_2-2-15.doc

Size

460.5 KB

Format

Microsoft Word

Checksum (MD5)

5607f620513af0ef69bea578f2471852

Owning collection
Biomolecular and Biomedical Science Research Collection

Item descriptive metadata is released under a CC-0 (public domain) license: https://creativecommons.org/public-domain/cc0/.
All other content is subject to copyright.

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