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A Clade II‐D Fungal Chimeric Diterpene Synthase from Colletotrichum gloeosporioides Produces Dolasta‐1(15),8‐diene
Author(s) -
Bian Guangkai,
Rinkel Jan,
Wang Zhangqian,
Lauterbach Lukas,
Hou Anwei,
Yuan Yujie,
Deng Zixin,
Liu Tiangang,
Dickschat Jeroen S.
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.201809954
Subject(s) - diterpene , atp synthase , terpene , colletotrichum gloeosporioides , stereochemistry , biology , terpenoid , clade , absolute configuration , enzyme , chemistry , botany , biochemistry , gene , phylogenetics
Based on a terpenoid overproduction platform in yeast for genome mining, a chimeric diterpene synthase from the endophytic fungus Colletotrichum gloeosporioides ES026 was characterized as the (5 R ,12 R ,14 S )‐dolasta‐1(15),8‐diene synthase. The absolute configuration was independently verified through the use of enantioselectively deuterated terpene precursors, which unequivocally established the predicted C1‐III‐IV cyclization mode for this first characterized clade II‐D enzyme. Extensive isotopic labeling experiments and isolation of the intermediate (1 R )‐δ‐araneosene supported the proposed cyclization mechanism.