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Diterpene Biosynthesis in Catenulispora acidiphila : On the Mechanism of Catenul‐14‐en‐6‐ol Synthase
Author(s) -
Li Geng,
Guo YueWei,
Dickschat Jeroen S.
Publication year - 2021
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.202014180
Subject(s) - diterpene , stereochemistry , terpene , enantioselective synthesis , chemistry , sesquiterpene , atp synthase , biosynthesis , terpenoid , reactivity (psychology) , organic chemistry , enzyme , catalysis , medicine , alternative medicine , pathology
A new diterpene synthase from the actinomycete Catenulispora acidiphila was identified and the structures of its products were elucidated, including the absolute configurations by an enantioselective deuteration approach. The mechanism of the cationic terpene cyclisation cascade was deeply studied through the use of isotopically labelled substrates and of substrate analogues with partially blocked reactivity, resulting in derailment products that gave further insights into the intermediates along the cascade. Their chemistry was studied, leading to the biomimetic synthesis of a diterpenoid analogue of a brominated sesquiterpene known from the red seaweed Laurencia microcladia.