Issue 23, 2024

β-Terrecyclene synthase constructs the quadrane backbone in terrecyclic acid biosynthesis

Abstract

Quadrane sesquiterpenes featuring a distinctive tricyclic skeleton exhibit potent antimicrobial and anticancer activities. Although extensive studies have attempted to reveal the multistep carbocation rearrangement involved in the formation of the tricyclic quadrane scaffold, the exact biosynthetic pathway and chemical logic to generate the quadrane structure remains mysterious. Here we identified a novel sesquiterpene synthase that is capable of generating β-terrecyclene possessing the quadrane scaffold and characterized the biosynthetic pathway of a representative fungal quadrane terrecyclic acid. Further mutagenesis coupled with isotopically sensitive branching studies of this β-terrecyclene synthase provided insight into the mechanism involved in the formation of the quadrane scaffold.

Graphical abstract: β-Terrecyclene synthase constructs the quadrane backbone in terrecyclic acid biosynthesis

Supplementary files

Article information

Article type
Edge Article
Submitted
20 feb 2024
Accepted
18 apr 2024
First published
25 apr 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 8750-8755

β-Terrecyclene synthase constructs the quadrane backbone in terrecyclic acid biosynthesis

Y. Song, W. Wang, J. Yang, D. Gao, J. M. Billingsley, S. Wang, Y. Zhu, J. Wang, J. Ju, Y. Yan and Y. Tang, Chem. Sci., 2024, 15, 8750 DOI: 10.1039/D4SC01208A

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