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

Authors

Chiraz Soumia M. Amrine, Arkansas Tech UniversityFollow
Jessica L. Long, The University of North Carolina at Greensboro
Huzefa A. Raja, The University of North Carolina at Greensboro
Steven J. Kurina, University of Illinois at Chicago
Joanna E. Burdette, University of Illinois at Chicago
Cedric Pearce J., Mycosynthetix, Inc.
Nicholas H. Oberlies, The University of North Carolina at Greensboro

Document Type

Article

Publication Date

11-22-2019

Department

Physical & Earth Sciences

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.

DOI

10.1021/acs.jnatprod.9b00711

First Page

3104

Last Page

3110

Volume

82

Issue

11

Publication Title

Journal of Natural Products

ISSN

01633864

Comments

At the time of publication, Chiraz Soumia M. Amrine was affiliated with The University of North Carolina at Greensboro.

Recommended Citation

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.