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Molecular Basis of Elansolid Biosynthesis: Evidence for an Unprecedented Quinone Methide Initiated Intramolecular Diels–Alder Cycloaddition/Macrolactonization
Author(s) -
Dehn Richard,
Katsuyama Yohei,
Weber Arne,
Gerth Klaus,
Jansen Rolf,
Steinmetz Heinrich,
Höfle Gerhard,
Müller Rolf,
Kirschning Andreas
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201006880
Subject(s) - intramolecular force , cycloaddition , polyketide , biosynthesis , stereochemistry , secondary metabolite , chemistry , gene , biochemistry , catalysis
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.