Molecular basis of elansolid biosynthesis: Evidence for an unprecedented quinone methide initiated intramolecular diels-alder cycloaddition/ macrolactonization

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Autoren

  • Richard Dehn
  • Yohei Katsuyama
  • Arne Weber
  • Klaus Gerth
  • Rolf Jansen
  • Heinrich Steinmetz
  • Gerhard Höfle
  • Rolf Müller
  • Andreas Kirschning

Externe Organisationen

  • Helmholtz-Zentrum für Infektionsforschung GmbH (HZI)
Forschungs-netzwerk anzeigen

Details

Titel in ÜbersetzungMolekulare Grundlage für die Biosynthese von Elansolid: Beweise für eine einzigartige, durch ein Chinonmethid initiierte intramolekulare Diels-Alder-Cycloaddition/Makrolactonisierung
OriginalspracheEnglisch
Seiten (von - bis)3882-3887
Seitenumfang6
FachzeitschriftAngewandte Chemie
Jahrgang50
Ausgabenummer17
PublikationsstatusVeröffentlicht - 29 März 2011

Abstract

Total control: The key steps in the biosynthesis of elansolide A1, a new and structurally unique polyketide metabolite from the gliding bacterium Chitinophaga sancti, have been elucidated from feeding experiments, by analysis of the biosynthetic gene cluster, and through the synthesis of model substrates. These steps include an unprecedented dehydration reaction, an intramolecular Diels-Alder cycloaddition (IMDA), and an unusual macrolactonization.

ASJC Scopus Sachgebiete

Zitieren

Molecular basis of elansolid biosynthesis: Evidence for an unprecedented quinone methide initiated intramolecular diels-alder cycloaddition/ macrolactonization. / Dehn, Richard; Katsuyama, Yohei; Weber, Arne et al.
in: Angewandte Chemie , Jahrgang 50, Nr. 17, 29.03.2011, S. 3882-3887.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

Dehn R, Katsuyama Y, Weber A, Gerth K, Jansen R, Steinmetz H et al. Molecular basis of elansolid biosynthesis: Evidence for an unprecedented quinone methide initiated intramolecular diels-alder cycloaddition/ macrolactonization. Angewandte Chemie . 2011 Mär 29;50(17):3882-3887. doi: 10.1002/anie.201006880, 10.1002/ange.201006880
Download
@article{cd74c4e4ece449198b2bf61327eeab97,
title = "Molecular basis of elansolid biosynthesis: Evidence for an unprecedented quinone methide initiated intramolecular diels-alder cycloaddition/ macrolactonization",
abstract = "Total control: The key steps in the biosynthesis of elansolide A1, a new and structurally unique polyketide metabolite from the gliding bacterium Chitinophaga sancti, have been elucidated from feeding experiments, by analysis of the biosynthetic gene cluster, and through the synthesis of model substrates. These steps include an unprecedented dehydration reaction, an intramolecular Diels-Alder cycloaddition (IMDA), and an unusual macrolactonization.",
keywords = "biosynthesis, intramolecular Diels-Alder reaction, macrocyclizations, polyketides, quinone methides",
author = "Richard Dehn and Yohei Katsuyama and Arne Weber and Klaus Gerth and Rolf Jansen and Heinrich Steinmetz and Gerhard H{\"o}fle and Rolf M{\"u}ller and Andreas Kirschning",
year = "2011",
month = mar,
day = "29",
doi = "10.1002/anie.201006880",
language = "English",
volume = "50",
pages = "3882--3887",
journal = "Angewandte Chemie ",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "17",

}

Download

TY - JOUR

T1 - Molecular basis of elansolid biosynthesis

T2 - Evidence for an unprecedented quinone methide initiated intramolecular diels-alder cycloaddition/ macrolactonization

AU - Dehn, Richard

AU - Katsuyama, Yohei

AU - Weber, Arne

AU - Gerth, Klaus

AU - Jansen, Rolf

AU - Steinmetz, Heinrich

AU - Höfle, Gerhard

AU - Müller, Rolf

AU - Kirschning, Andreas

PY - 2011/3/29

Y1 - 2011/3/29

N2 - Total control: The key steps in the biosynthesis of elansolide A1, a new and structurally unique polyketide metabolite from the gliding bacterium Chitinophaga sancti, have been elucidated from feeding experiments, by analysis of the biosynthetic gene cluster, and through the synthesis of model substrates. These steps include an unprecedented dehydration reaction, an intramolecular Diels-Alder cycloaddition (IMDA), and an unusual macrolactonization.

AB - Total control: The key steps in the biosynthesis of elansolide A1, a new and structurally unique polyketide metabolite from the gliding bacterium Chitinophaga sancti, have been elucidated from feeding experiments, by analysis of the biosynthetic gene cluster, and through the synthesis of model substrates. These steps include an unprecedented dehydration reaction, an intramolecular Diels-Alder cycloaddition (IMDA), and an unusual macrolactonization.

KW - biosynthesis

KW - intramolecular Diels-Alder reaction

KW - macrocyclizations

KW - polyketides

KW - quinone methides

UR - http://www.scopus.com/inward/record.url?scp=79954622948&partnerID=8YFLogxK

U2 - 10.1002/anie.201006880

DO - 10.1002/anie.201006880

M3 - Article

C2 - 21472917

AN - SCOPUS:79954622948

VL - 50

SP - 3882

EP - 3887

JO - Angewandte Chemie

JF - Angewandte Chemie

SN - 1433-7851

IS - 17

ER -

Von denselben Autoren