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Modular chemoenzymatic synthesis of terpenes and their analogues

Johnson, Luke A., Dunbabin, Alice, Benton, Jennifer C. R., Mart, Robert J. and Allemann, Rudolf K. 2020. Modular chemoenzymatic synthesis of terpenes and their analogues. Angewandte Chemie International Edition 59 (22) , pp. 8486-8490. 10.1002/anie.202001744
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Abstract

Non‐natural terpenoids offer potential as pharmaceuticals and agrochemicals. However, their chemical syntheses are often long, complex, and not easily amenable to large‐scale production. Herein, we report a modular chemoenzymatic approach to synthesize terpene analogues from diphosphorylated precursors produced in quantitative yields. Through the addition of prenyl transferases, farnesyl diphosphates, (2E,6E)‐FDP and (2Z,6Z)‐FDP, were isolated in greater than 80 % yields. The synthesis of 14,15‐dimethyl‐FDP, 12‐methyl‐FDP, 12‐hydroxy‐FDP, homo‐FDP, and 15‐methyl‐FDP was also achieved. These modified diphosphates were used with terpene synthases to produce the unnatural sesquiterpenoid semiochemicals (S)‐14,15‐dimethylgermacrene D and (S)‐12‐methylgermacrene D as well as dihydroartemisinic aldehyde. This approach is applicable to the synthesis of many non‐natural terpenoids, offering a scalable route free from repeated chain extensions and capricious chemical phosphorylation reactions.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Wiley
ISSN: 1433-7851
Funders: EPSRC and BBSRC
Date of First Compliant Deposit: 3 April 2020
Date of Acceptance: 26 February 2020
Last Modified: 08 Sep 2020 10:00
URI: http://orca-mwe.cf.ac.uk/id/eprint/130759

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