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

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.

SUBMITTER: Struwe H

PROVIDER: S-EPMC10714441 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature

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

Struwe Henry H Schrödter Finn F Spinck Hanke H Kirschning Andreas A

Organic letters 20231127 48

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 f ...[more]

PMID: 38011332

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