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.
et al.
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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