Stereoselective deprotonation installs an unusual Z-8,9 double bond during biosynthesis of the diterpene pheromone sobralene

Da Silva, Igor F. P.; Ducker, Charles; Pickett, John A.; Santana, Antônio E. G.; Oldham, Neil J.

Abstract

A terpene synthase from the sandfly Lutzomyia longipalpis, catalyses stereoselective removal of the pro-S proton from C8 of geranylgeranyl diphosphate to generate the characteristic (Z)-8,9 double bond seen in the diterpene pheromone sobralene. Retention of deuterium in structurally related minor products demonstrates that they are not produced via sobralene, but are made directly by the enzyme.

Citation

Da Silva, I. F. P., Ducker, C., Pickett, J. A., Santana, A. E. G., & Oldham, N. J. (2025). Stereoselective deprotonation installs an unusual Z-8,9 double bond during biosynthesis of the diterpene pheromone sobralene. Chemical Communications, 2025(64), 12026–12029. https://doi.org/10.1039/d5cc03298a

• Journal Article Type: Article
• Acceptance Date: Jul 1, 2025
• Online Publication Date: Jul 7, 2025
• Publication Date: Aug 18, 2025
• Deposit Date: Jul 14, 2025
• Publicly Available Date: Jul 16, 2025
• Journal: Chemical Communications
• Print ISSN: 1359-7345
• Electronic ISSN: 1364-548X
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 2025
• Issue: 64
• Pages: 12026–12029
• DOI: https://doi.org/10.1039/d5cc03298a
• Public URL: https://nottingham-repository.worktribe.com/output/51612586
• Publisher URL: https://pubs.rsc.org/en/content/articlelanding/2025/cc/d5cc03298a