Sesquiterpene Backbones Generated by Sesquiterpene Cyclases: Formation of iso-Caryolan-1-ol and an Isoclovane

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Original languageEnglish
Pages (from-to)8575-8579
Number of pages5
JournalOrganic letters
Volume25
Issue number48
Early online date27 Nov 2023
Publication statusPublished - 8 Dec 2023

Abstract

New sesquiterpene backbones are accessible after incubation of caryolan-synthase (GcoA) and presilphiperfolan-8-β-ol synthase (BcBOT2) with a non-natural farnesyldiphosphate in which the central olefinic double bond is isomerized toward the methyl group. Two newly formed sesquiterpenoids are reported, a constitutional isomer of caryolan-1-ol (3), which we name iso-caryolan-1-ol (17), and the first terpenoid based on the isoclovane ring skeleton generated enzymatically thus far.

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Sesquiterpene Backbones Generated by Sesquiterpene Cyclases: Formation of iso-Caryolan-1-ol and an Isoclovane. / Struwe, Henry; Schrödter, Finn; Spinck, Hanke et al.
In: Organic letters, Vol. 25, No. 48, 08.12.2023, p. 8575-8579.

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Struwe H, Schrödter F, Spinck H, Kirschning A. Sesquiterpene Backbones Generated by Sesquiterpene Cyclases: Formation of iso-Caryolan-1-ol and an Isoclovane. Organic letters. 2023 Dec 8;25(48):8575-8579. Epub 2023 Nov 27. doi: 10.1021/acs.orglett.3c03383
Struwe, Henry ; Schrödter, Finn ; Spinck, Hanke et al. / Sesquiterpene Backbones Generated by Sesquiterpene Cyclases : Formation of iso-Caryolan-1-ol and an Isoclovane. In: Organic letters. 2023 ; Vol. 25, No. 48. pp. 8575-8579.
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AU - Struwe, Henry

AU - Schrödter, Finn

AU - Spinck, Hanke

AU - Kirschning, Andreas

N1 - Funding information: We thank Dr. Jörn Droste (Leibniz University Hannover) for expert support in all issues concerning NMR spectroscopic analysis.

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