Molecules 2010, 15(3), 1309-1323; doi:10.3390/molecules15031309

Stereodynamic Investigation of Labile Stereogenic Centres in Dihydroartemisinin

1,* email, 1,* email, 1, 1, 1, 2email, 2 and 2
Received: 1 January 2010; in revised form: 25 January 2010 / Accepted: 4 March 2010 / Published: 5 March 2010
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: Since its identification in the early 1970s, artemisinin, as well as semi-synthetic derivatives and synthetic trioxanes, have been used in malaria therapy. Reduction of artemisinin by NaBH4 produced dihydroartemisinin (DHA), and yielded a new stereochemically labile centre at C-10, which, in turn, provided two interconverting lactol hemiacetal epimers (namely a and b), whose rate of interconversion depends on buffer, pH, and solvent polarity. Since interconversion of the two epimers occurred on a chromatographic time-scale, this prompted a thorough investigation of the phenomenon as a crucial requisite of any analytical method aimed at quantitating this family of drugs. In this critical review we discuss the current importance of the on-column epimerization of DHA in the development of analytical methods aimed at quantifying the drug, with the purpose of identifying the optimal conditions to minimize on-column epimerization while achieving the best selectivity and efficiency of the overall separation.
Keywords: Dihydroartemisinin (DHA); on-column epimerization; cryo-HPLC; dynamic HPLC (DHPLC); computer simulation
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MDPI and ACS Style

D’Acquarica, I.; Gasparrini, F.; Kotoni, D.; Pierini, M.; Villani, C.; Cabri, W.; Di Mattia, M.; Giorgi, F. Stereodynamic Investigation of Labile Stereogenic Centres in Dihydroartemisinin. Molecules 2010, 15, 1309-1323.

AMA Style

D’Acquarica I, Gasparrini F, Kotoni D, Pierini M, Villani C, Cabri W, Di Mattia M, Giorgi F. Stereodynamic Investigation of Labile Stereogenic Centres in Dihydroartemisinin. Molecules. 2010; 15(3):1309-1323.

Chicago/Turabian Style

D’Acquarica, Ilaria; Gasparrini, Francesco; Kotoni, Dorina; Pierini, Marco; Villani, Claudio; Cabri, Walter; Di Mattia, Michela; Giorgi, Fabrizio. 2010. "Stereodynamic Investigation of Labile Stereogenic Centres in Dihydroartemisinin." Molecules 15, no. 3: 1309-1323.

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