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Stereodynamic Investigation of Labile Stereogenic Centres in Dihydroartemisinin
AbstractSince 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.
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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.View more citation formats
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.