Regiodivergent NC and NN Aryl Coupling Reactions of Indoloterpenes and Cycloether Formation Mediated by a Single Bacterial Flavoenzyme

Martin Baunach, Ling Ding, Torsten Bruhn, Gerhard Bringmann, Christian Hertweck

Research output: Contribution to journalJournal article

Abstract

Radical diversification: Through the discovery of diverse indolosesquiterpene dimers in a strain heterologously expressing the xiamycin biosynthesis genes, the analysis of mutants, and biotransformation studies, it has been inferred that a single flavoprotein mediates N-C and N-N aryl coupling reactions, as well as the formation of a cyclic ether (oxiamycin). Synthetic emulation of this unusual transformation provides evidence for a radical-based mechanism. 
Original languageEnglish
JournalAngewandte chemie-international edition
Volume52
Issue number34
Pages (from-to)9040-9043
Number of pages4
ISSN1433-7851
DOIs
Publication statusPublished - 2013
Externally publishedYes

Keywords

  • Alkaloids
  • Aryl Coupling
  • Flavoproteins
  • Indolosesquiterpenes
  • Radicals

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