Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 3, Pages 1488-1492Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202014180
Keywords
biosynthesis; enzyme mechanisms; isotopes; substrate analogues; terpenoids
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Funding
- DFG [DI1536/7-2]
- Natural Science foundation of China [81991521, 81520108028]
- CAS-DAAD Doctoral Joint Scholarship Program
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A new diterpene synthase was identified from the actinomycete Catenulispora acidiphila, and its products were elucidated, leading to the biomimetic synthesis of a diterpenoid analogue of a brominated sesquiterpene known from the red seaweed Laurencia microcladia, through in-depth studies of the mechanism and chemistry of cationic terpene cyclisation cascade.
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.
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