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Novel fluorinated lipopeptides from Bacillus sp. CS93 via precursor-directed biosynthesis
Neil K O'Connor1, Alex S Hudson, Steven L Cobb
1UCD School of Biomolecular and Biomedical Science, University College Dublin, Belfield, Dublin 4, Ireland.
Amino Acids
|September 7, 2014
Summary
Researchers created novel fluorinated fengycin lipopeptides by incorporating fluorinated amino acids into Bacillus sp. CS93. These new compounds showed antifungal activity comparable to existing fengycins.
Area of Science:
- Biochemistry
- Synthetic Biology
- Microbiology
Background:
- Fengycin is a lipopeptide produced by Bacillus species with antifungal properties.
- Modifying natural products can lead to enhanced or novel biological activities.
- Incorporation of fluorine atoms into organic molecules can alter their physicochemical and biological properties.
Purpose of the Study:
- To synthesize novel fluorinated fengycin derivatives.
- To investigate the incorporation of fluorinated amino acids into fengycin.
- To evaluate the antifungal activity of the synthesized fluorinated fengycins.
Main Methods:
- Incubation of Bacillus sp. CS93 with 3-fluoro-L-tyrosine.
- (19)F NMR and tandem mass spectrometry for detection of fluorinated fengycins.
- Synthesis of fluorinated tyrosine derivatives using Negishi cross-coupling.
- Antifungal activity assays against Trichophyton rubrum.
Main Results:
- Detection of novel mono- and di-fluorinated fengycins.
- Confirmation of fluorinated amino acid incorporation into the fengycin structure.
- Fluorinated fengycins exhibited antifungal activity similar to non-fluorinated fengycins against Trichophyton rubrum.
Conclusions:
- Bacillus sp. CS93 can incorporate fluorinated amino acids into fengycin.
- Novel fluorinated fengycin derivatives can be generated through metabolic engineering.
- Fluorination did not significantly alter the antifungal potency of fengycin against Trichophyton rubrum.
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