International collaboration in the chemistry of alkaloid natural product biosynthesis
| Full text | |
| Author(s): |
Newmister, Sean A.
;
Gober, Claire M.
;
Romminger, Stelamar
;
Yu, Fengan
;
Tripathi, Ashootosh
;
Parra, Lizbeth Lorena L.
;
Williams, Robert M.
;
Berlinck, Roberto G. S.
;
Joullie, Madeleine M.
;
Sherman, David H.
Total Authors: 10
|
| Document type: | Journal article |
| Source: | Journal of the American Chemical Society; v. 138, n. 35, p. 11176-11184, SEP 7 2016. |
| Web of Science Citations: | 14 |
| Abstract | |
Indole alkaloids are a diverse class of natural products known for their wide range of biological activities and complex chemical structures. Rarely observed in this class are indolic nitrones, such as avrainvillamide and waikialoid, which possess potent bioactivities. Herein the oxa gene cluster from the marine-derived fungus Penicillium oxalicum F30 is described along with the characterization of OxaD, a flavin-dependent oxidase that generates roquefortine L, a nitrone-bearing intermediate in the biosynthesis of oxaline. Nitrone functionality in roquefortine L was confirmed by spectroscopic methods and 1,3-dipolar cycloaddition with methyl acrylate. OxaD is a versatile biocatalyst that converts an array of semisynthetic roquefortine C derivatives bearing indoline systems to their respective nitrones. This work describes the first implementation of a nitrone synthase as a biocatalyst and establishes a novel platform for late-stage diversification of a range of complex natural products. (AU) | |
| FAPESP's process: | 13/50228-8 - Biodiversity components, and its metabolic characters, of Brazilian Islands |
| Grantee: | Roberto Gomes de Souza Berlinck |
| Support type: | BIOTA-FAPESP Program - Thematic Grants |
| FAPESP's process: | 14/05670-7 - Sabbatical project proposal at the professor David H. Sherman research group |
| Grantee: | Roberto Gomes de Souza Berlinck |
| Support type: | Scholarships abroad - Research |
| FAPESP's process: | 12/50026-3 - International collaboration in the chemistry of alkaloid natural product biosynthesis |
| Grantee: | Roberto Gomes de Souza Berlinck |
| Support type: | Regular Research Grants |