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  5. Production of the Novel Lipopeptide Antibiotic Trifluorosurfactin via Precursor-Directed Biosynthesis
 
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Production of the Novel Lipopeptide Antibiotic Trifluorosurfactin via Precursor-Directed Biosynthesis

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Download Revision_Production_of_the_Novel_Lipopeptide_Antibiotic_Trifluorosurfactin_21-6-12.docx1.89 MB
Author(s)
O'Connor, Neil K. 
Rai, Dilip K. 
Clark, Benjamin R. 
Murphy, Cormac D. 
Uri
http://hdl.handle.net/10197/4298
Date Issued
November 2012
Date Available
01T10:24:36Z May 2013
Abstract
Incorporation of fluorine into antibiotics can moderate their biological activity, lipophilicity and metabolic stability. The introduction of fluorine into an antimicrobial lipopeptide produced by Bacillus sp. CS93 via precursor-directed biosynthesis is described. The lipopeptide surfactin is synthesised non-ribosomally by various Bacillus species and is known for its biological activity. Administering 4,4,4-trifluoro-dl-valine to cultures of Bacillus sp. CS93 results in the formation of trifluorosurfactin in quantities sufficient for detection by LC–MS/MS. 19F NMR analysis of the culture supernatant revealed that the bulk of the fluorinated amino acid was transformed and thus was unavailable for incorporation into surfactin. Detection of ammonia, and MS analysis indicated that the transformation proceeds with deamination and reduction of the keto acid, yielding 4,4,4-trifluoro-2-hydroxy-3-methylbutanoic acid.
Other Sponsorship
IRCSET Enterprise Partnership
Type of Material
Journal Article
Publisher
Elsevier
Journal
Journal of Fluorine Chemistry
Volume
143
Start Page
210
End Page
215
Copyright (Published Version)
2012 Elsevier B.V.
Keywords
  • Bacillus

  • Non-ribosomal peptide...

  • Fluorine

  • Biosynthesis

DOI
10.1016/j.jfluchem.2012.06.033
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/
Owning collection
Biomolecular and Biomedical Science Research Collection
Scopus© citations
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