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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. ORCID: https://orcid.org/0000-0002-1008-6595, Santana, Antônio E. G. and Oldham, Neil J. 2025. Stereoselective deprotonation installs an unusual Z -8,9 double bond during biosynthesis of the diterpene pheromone sobralene † ‡. Chemical Communications 10.1039/d5cc03298a

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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.

Item Type: Article
Date Type: Published Online
Status: In Press
Schools: Schools > Chemistry
Additional Information: License information from Publisher: LICENSE 1: URL: https://creativecommons.org/licenses/by/3.0/, Start Date: 2025-07-07
Publisher: Royal Society of Chemistry
ISSN: 1359-7345
Date of First Compliant Deposit: 15 July 2025
Date of Acceptance: 1 July 2025
Last Modified: 15 Jul 2025 15:45
URI: https://orca.cardiff.ac.uk/id/eprint/179854

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