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Total synthesis and biological investigation of (-)-artemisinin : the antimalarial activity of artemisinin is not stereospecific

Krieger, Johannes and Smeilus, Toni and Kaiser, Marcel and Seo, Ean-Jeong and Efferth, Thomas and Giannis, Athanassios. (2018) Total synthesis and biological investigation of (-)-artemisinin : the antimalarial activity of artemisinin is not stereospecific. Angewandte Chemie, 57 (27). pp. 8293-8296.

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Official URL: https://edoc.unibas.ch/69843/

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Abstract

Here, we describe an efficient and diversity-oriented entry to both (-)-artemisinin (1) and its natural antipode (+)-artemisinin, starting from commercially and readily available S-(+)- and R-(-)-citronellene, respectively. Subsequently, we answered the still open question regarding the specificity of artemisinins action. By using a drug-sensitive Plasmodium falciparum NF54 strain, we showed that the antimalarial activity of artemisinin is not stereospecific. Our straightforward and biomimetic approach to this natural endoperoxide enables the synthesis of artemisinin derivatives that are not accessible through applying current methods and may help to address the problem of emerging resistance of Plasmodium falciparum towards artemisinin.
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology (MPI) > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Kaiser, Marcel
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Wiley-VCH
ISSN:0570-0833
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:20 Mar 2019 13:31
Deposited On:20 Mar 2019 13:31

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