Novel fluorinated lipopeptides from Bacillus sp. CS93 via precursor-directed biosynthesis

O’Connor, N.K.; Hudson, A.S.; Cobb, S.L.; O’Neil, D.; Robertson, J.; Duncan, V.; Murphy, C.D.

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.

Citation

O’Connor, N., Hudson, A., Cobb, S., O’Neil, D., Robertson, J., Duncan, V., & Murphy, C. (2014). Novel fluorinated lipopeptides from Bacillus sp. CS93 via precursor-directed biosynthesis. Amino Acids, 46(12), 2745-2752. https://doi.org/10.1007/s00726-014-1830-z

• Journal Article Type: Article
• Acceptance Date: Aug 21, 2014
• Online Publication Date: Sep 6, 2014
• Publication Date: Dec 1, 2014
• Deposit Date: Jan 15, 2015
• Publicly Available Date: Jul 17, 2018
• Journal: Amino Acids
• Print ISSN: 0939-4451
• Electronic ISSN: 1438-2199
• Publisher: Springer
• Peer Reviewed: Peer Reviewed
• Volume: 46
• Issue: 12
• Pages: 2745-2752
• DOI: https://doi.org/10.1007/s00726-014-1830-z
• Keywords: Antibiotic, Bacillus, Fluorine, Tyrosine.
• Related Public URLs: https://researchrepository.ucd.ie/handle/10197/7138