2. Academic Validation
  3. Engineering Fluorine into Verticillins (Epipolythiodioxopiperazine Alkaloids) via Precursor-Directed Biosynthesis

Engineering Fluorine into Verticillins (Epipolythiodioxopiperazine Alkaloids) via Precursor-Directed Biosynthesis

  • J Nat Prod. 2019 Nov 22;82(11):3104-3110. doi: 10.1021/acs.jnatprod.9b00711.
Chiraz Soumia M Amrine 1,  Jessica L Long 1,  Huzefa A Raja 1,  Steven J Kurina 2,  Joanna E Burdette 2,  Cedric J Pearce 3,  Nicholas H Oberlies 1
Affiliations

Affiliations

  • 1 Department of Chemistry and Biochemistry , University of North Carolina at Greensboro , Greensboro , North Carolina 27402 , United States.
  • 2 Department of Pharmaceutical Sciences , University of Illinois at Chicago , Chicago , Illinois 60612 , United States.
  • 3 Mycosynthetix Inc. , 505 Meadowlands Drive, Suite 103 , Hillsborough , North Carolina 27278 , United States.
PMID: 31633350 DOI: 10.1021/acs.jnatprod.9b00711
Abstract

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.

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