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An efficient chemoenzymatic synthesis of dihydroartemisinic aldehyde

Demiray, Melodi, Tang, Xiaoping, Wirth, Thomas, Faraldos, Juan A. and Allemann, Rudolf K. 2017. An efficient chemoenzymatic synthesis of dihydroartemisinic aldehyde. Angewandte Chemie International Edition 56 (15) , pp. 4347-4350. 10.1002/anie.201609557

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Artemisinin from the plant Artemisia annua is the most potent pharmaceutical for the treatment of malaria. In the plant, the sesquiterpene cyclase amorphadiene synthase, a cytochrome- dependent CYP450, and an aldehyde reductase convert farnesyl diphosphate (FDP) into dihydroartemisinic aldehyde (DHAAl), which is a key intermediate in the biosynthesis of artemisinin and a semisynthetic precursor for its chemical synthesis. Here, we report a chemoenzymatic process that is able to deliver DHAAl using only the sesquiterpene synthase from a carefully designed hydroxylated FDP derivative. This process, which reverses the natural order of cyclization of FDP and oxidation of the sesquiterpene hydrocarbon, provides a significant improvement in the synthesis of DHAAl and demonstrates the potential of substrate engineering in the terpene synthase mediated synthesis of highvalue natural products.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Uncontrolled Keywords: artemisinin; chemoenzymatic synthesis; sesquiterpenoids; substrate engineering; synthetic biology
Publisher: Wiley
ISSN: 1433-7851
Date of First Compliant Deposit: 22 March 2017
Date of Acceptance: 19 January 2017
Last Modified: 21 Aug 2022 08:12

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