ArticleJournal of the American Chemical Society2024
Sesquiterpene Cyclase BcBOT2 Promotes the Unprecedented Wagner-Meerwein Rearrangement of the Methoxy Group.
Article in Journal of the American Chemical Society, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Introducing Small Rings into Farnesyl Pyrophosphates Paves the Way for the Enzymatic Generation of Unnatural Sesquiterpene Scaffolds.Journal of the American Chemical Society · 2026Article
- Chemoenzymatic Synthesis of Structurally Diverse Terpenoids from Farnesyl Pyrophosphates Modified at the Central Alkene Unit.Journal of the American Chemical Society · 2026Article
- Mechanistic Characterisation of a Diterpene Synthase for Chryseojoostenes A-E from Chryseobacterium Joostei.Angewandte Chemie (International ed. in English) · 2025Article
- Eremophilane-Type Sesquiterpenoids from FungusMolecules (Basel, Switzerland) · 2025Article
- Divergent Synthesis of Polycyclic N‑Heterocycles via Controllable Cyclization of Divinylallenes Catalyzed by Copper and Gold.JACS Au · 2025Article
- Chemoenzymatic Generation of Thio-analogues of δ-Cadinene, δ-Cadinol, and a Thio-diquinane Using 8-Thio-farnesylpyrophosphate.Journal of natural products · 2025Article
- Enzyme-Catalysed Formation of Hydrocarbon Scaffolds from Geranylgeranyl Diphosphate Analogs with Shifted Double Bonds.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Engineering terpene synthases and their substrates for the biocatalytic production of terpene natural products and analogues.Chemical communications (Cambridge, England) · 2025Review
- Chemoenzymatic Formation of Oxa-Terpenoids by Sesqui- and Diterpene Synthase-Mediated Biotransformations with 9-Oxy-FPP Ether Derivatives.Biochemistry · 2025Article
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Authors and funding
9 authors.
Funding
Abstract
Presilphiperfolan-8β-ol synthase (BcBOT2), a substrate-promiscuous sesquiterpene cyclase (STC) of fungal origin, is capable of converting two new farnesyl pyrophosphate (FPP) derivatives modified at C7 of farnesyl pyrophosphate (FPP) bearing either a hydroxymethyl group or a methoxymethyl group. These substrates were chosen based on a computationally generated model. Biotransformations yielded five new oxygenated terpenoids. Remarkably, the formation of one of these tricyclic products can only be explained by a cationically induced migration of the methoxy group, presumably via a Meerwein-salt intermediate, unprecedented in synthetic chemistry and biosynthesis. The results show the great principle and general potential of terpene cyclases for mechanistic studies of unusual cation chemistry and for the creation of new terpene skeletons.
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