Ruptenes: A Family of Terpene Analogs Give Insight into Cyclisation Mechanisms by Cascade Disruption

Author:

Gu Binbin1,Dickschat Jeroen S.1ORCID

Affiliation:

1. Kekulé Institute of Organic Chemistry and Biochemistry University of Bonn Gerhard-Domagk-Straße 1 53121 Bonn Germany

Abstract

AbstractThe terpenoid substrate analogs (7R)‐6,7‐dihydrogeranylgeranyl diphosphate (6,7‐dihydro‐GGPP) and (7R)‐6,7‐dihydrogeranylfarnesyl diphosphate (6,7‐dihydro‐GFPP) were synthesised from (S)‐citronellol and enzymatically converted with nine diterpene and two sesterterpene synthases, respectively. In two cases the substrate analogs were converted into diterpenes in cyclisation reactions corresponding to those observed for the native substrate GGPP, while the cyclisation cascade was disrupted or redirected in the other nine cases, leading to products that were named ruptenes. Several of the isolated ruptenes represent deprotonation products of cationic intermediates that are analogs of the intermediates proposed along the cyclisation cascades for the native substrates GGPP or GFPP, thus giving insights into the complex reaction mechanisms of terpene synthase mediated biosynthesis.

Funder

Deutsche Forschungsgemeinschaft

Publisher

Wiley

Subject

General Chemistry,Catalysis

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