Exploiting the Synthetic Potential of Sesquiterpene Cyclases for Generating Unnatural Terpenoids

Clara Oberhauser; Vanessa Harms; Katja Seidel; Benjamin Schröder; Kimia Ekramzadeh; Sascha Beutel; Sven Winkler; Lukas Lauterbach; Jeroen S Dickschat; Andreas Kirschning

doi:10.1002/anie.201805526

Exploiting the Synthetic Potential of Sesquiterpene Cyclases for Generating Unnatural Terpenoids

Angew Chem Int Ed Engl. 2018 Sep 3;57(36):11802-11806. doi: 10.1002/anie.201805526. Epub 2018 Aug 7.

Affiliations

¹ Institute of Organic Chemistry and Center of Biomolecular Drug Research (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, 30167, Hannover, Germany.
² Institute of Technical Chemistry and Center of Biomolecular Drug Research (BMWZ), Leibniz Universität Hannover, Callinstr. 5, 30167, Hannover, Germany.
³ Symrise AG, Mühlenfeldstrasse 1, 37603, Holzminden, Germany.
⁴ Kekulé-Institute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Straße 1, 53121, Bonn, Germany.

PMID: 29953712
DOI: 10.1002/anie.201805526

Abstract

The substrate flexibility of eight purified sesquiterpene cyclases was evaluated using six new heteroatom-modified farnesyl pyrophosphates, and the formation of six new heteroatom-modified macrocyclic and tricyclic sesquiterpenoids is described. GC-O analysis revealed that tricyclic tetrahydrofuran exhibits an ethereal, peppery, and camphor-like olfactoric scent.

Keywords: biocatalysis; farnesyl pyrophosphates; scent compounds; terpene cyclases; terpenoids.