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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

OxaD: A Versatile Indolic Nitrone Synthase from the Marine-Derived Fungus Penicillium oxalicum F30

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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: 12

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: 12/50026-3 - International collaboration in the chemistry of alkaloid natural product biosynthesis
Grantee:Roberto Gomes de Souza Berlinck
Support Opportunities: Regular Research 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 Opportunities: Scholarships abroad - Research
FAPESP's process: 13/50228-8 - Biodiversity components, and their metabolic characters, of Brazilian Islands: an integrated approach
Grantee:Roberto Gomes de Souza Berlinck
Support Opportunities: BIOTA-FAPESP Program - Thematic Grants