Novel fluorinated lipopeptides from Bacillus sp. CS93 via precursor-directed biosynthesis
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|Title:||Novel fluorinated lipopeptides from Bacillus sp. CS93 via precursor-directed biosynthesis||Authors:||O'Connor, Neil K.
Hudson, Alex S.
Cobb, Steven L.
Murphy, Cormac D.
|Permanent link:||http://hdl.handle.net/10197/7138||Date:||Dec-2014||Abstract:||While attempting to improve production of fluoro-iturin A in Bacillus sp. CS93 new mono- and di-fluorinated fengycins were detected in culture supernatants by 19F NMR and tandem mass spectrometry, after incubation of the bacterium with 3-fluoro-l-tyrosine. The fluorinated amino acid was presumably incorporated in place of one or both of the tyrosyl residues in fengycin. Investigations to generate additional new fluorinated derivatives were undertaken using commercially available fluorinated phenylalanines and 2-fluoro- and 2,3-difluoro-tyrosine that were synthesised by Negishi cross-coupling of iodoalanine and fluorinated bromo-phenols. The anti-fungal activity of the fluorinated lipopeptides was assayed against Trichophyton rubrum and found to be similar to that of the non-fluorinated metabolites.||Funding Details:||Irish Research Council||Type of material:||Journal Article||Publisher:||Springer||Copyright (published version):||2014 Springer-Verlag Wien||Keywords:||Antibiotic;Bacillus;Fluorine;Tyrosine||DOI:||10.1007/s00726-014-1830-z||Language:||en||Status of Item:||Peer reviewed|
|Appears in Collections:||Biomolecular and Biomedical Science Research Collection|
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