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

doi:10.1002/anie.201303733

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

University of Würzburg
Leibniz Institute for Natural Product Research and Infection Biology - Hans Knöll Institute

Research output: Contribution to journal › Journal article › Communication

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 language	English
Journal	Angewandte chemie-international edition
Volume	52
Issue number	34
Pages (from-to)	9040-9043
Number of pages	4
ISSN	1433-7851
DOIs	https://doi.org/10.1002/anie.201303733
Publication status	Published - 2013
Externally published	Yes

Keywords

Alkaloids
Aryl Coupling
Flavoproteins
Indolosesquiterpenes
Radicals

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10.1002/anie.201303733

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

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. ",

keywords = "Alkaloids, Aryl Coupling, Flavoproteins, Indolosesquiterpenes, Radicals",

author = "Martin Baunach and Ling Ding and Torsten Bruhn and Gerhard Bringmann and Christian Hertweck",

year = "2013",

doi = "10.1002/anie.201303733",

language = "English",

volume = "52",

pages = "9040--9043",

journal = "Angewandte chemie-international edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

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TY - JOUR

T1 - Regiodivergent NC and NN Aryl Coupling Reactions of Indoloterpenes and Cycloether Formation Mediated by a Single Bacterial Flavoenzyme

AU - Baunach, Martin

AU - Ding, Ling

AU - Bruhn, Torsten

AU - Bringmann, Gerhard

AU - Hertweck, Christian

PY - 2013

Y1 - 2013

N2 - 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.

AB - 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.

KW - Alkaloids

KW - Aryl Coupling

KW - Flavoproteins

KW - Indolosesquiterpenes

KW - Radicals

U2 - 10.1002/anie.201303733

DO - 10.1002/anie.201303733

M3 - Journal article

SN - 1433-7851

VL - 52

SP - 9040

EP - 9043

JO - Angewandte chemie-international edition

JF - Angewandte chemie-international edition

IS - 34

ER -

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

Abstract

Keywords

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