Engineering Fluorine into Verticillins (Epipolythiodioxopiperazine Alkaloids) via Precursor-Directed Biosynthesis
Precursor-directed biosynthesis was used to generate a series of fluorinated verticillins. The biosynthesis of these epipolythiodioxopiperazine alkaloids was monitored in situ via the droplet liquid microjunction surface sampling probe (droplet probe), and a suite of NMR and mass spectrometry data were used for their characterization. All analogues demonstrated nanomolar IC50 values vs a panel of cancer cell lines. This approach yielded new compounds that would be difficult to generate via synthesis.
Journal of Natural Products
Amrine, C. S. M., Long, J. L., Raja, H. A., Kurina, S. J., Burdette, J. E., Pearce, C. J., & Oberlies, N. H. (2019).Engineering Fluorine into Verticillins (Epipolythiodioxopiperazine Alkaloids) via Precursor-Directed Biosynthesis. Journal of Natural Products, 82(11):3104-3110. doi: 10.1021/acs.jnatprod.9b00711.