%0 Journal Article
%T Stereodynamic Investigation of Labile Stereogenic Centres in Dihydroartemisinin
%A Ilaria D¡¯Acquarica
%A Francesco Gasparrini
%A Dorina Kotoni
%A Marco Pierini
%A Claudio Villani
%A Walter Cabri
%A Michela Di Mattia
%A Fabrizio Giorgi
%J Molecules
%D 2010
%I MDPI AG
%R 10.3390/molecules15031309
%X 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.
%K Dihydroartemisinin (DHA)
%K on-column epimerization
%K cryo-HPLC
%K dynamic HPLC (DHPLC)
%K computer simulation
%U http://www.mdpi.com/1420-3049/15/3/1309