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Exploiting the Synthetic Potential of Sesquiterpene Cyclases for Generating Unnatural Terpenoids
Author(s) -
Oberhauser Clara,
Harms Vanessa,
Seidel Katja,
Schröder Benjamin,
Ekramzadeh Kimia,
Beutel Sascha,
Winkler Sven,
Lauterbach Lukas,
Dickschat Jeroen S.,
Kirschning Andreas
Publication year - 2018
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.201805526
Subject(s) - sesquiterpene , heteroatom , tricyclic , tetrahydrofuran , chemistry , terpenoid , stereochemistry , camphor , terpene , substrate (aquarium) , organic chemistry , ring (chemistry) , biology , ecology , solvent
The substrate flexibility of eight purified sesquiterpene cyclases was evaluated using six new heteroatom‐modified farnesyl pyrophosphates, and the formation of six new heteroatom‐modified macrocyclic and tricyclic sesquiterpenoids is described. GC‐O analysis revealed that tricyclic tetrahydrofuran exhibits an ethereal, peppery, and camphor‐like olfactoric scent.