Title of article :
Cyclodextrin-based liquid chromatographic enantiomeric separation of chiral dihydrofurocoumarins, an emerging class of medicinal compounds
Author/Authors :
Schumacher، نويسنده , , Douglas D. and Mitchell، نويسنده , , Clifford R. and Xiao، نويسنده , , Tom L. and Rozhkov، نويسنده , , Roman V. and Larock، نويسنده , , Richard C. and Armstrong، نويسنده , , Daniel W.، نويسنده ,
Issue Information :
روزنامه با شماره پیاپی سال 2003
Pages :
11
From page :
37
To page :
47
Abstract :
A set of 28 racemic dihydrofurocoumarins in which the stereogenic center is located in the furan ring have been synthesized. Currently no effective asymmetric synthesis of this class of compounds exists, although their enantiomers are produced biologically by certain plants. Their diverse medicinal properties are being investigated in several laboratories. The enantioselective separation of these dihydrofurocoumarins by three native and six derivatized cyclodextrins has been evaluated in the reversed-phase mode, the polar organic mode, and normal-phase mode. The hydroxypropyl-β-cyclodextrin is the most effective chiral stationary phase (CSP) at separating the dihydrofurocoumarins into enantiomers, showing some enantioselectivity for 22 dihydrofurocoumarins, and baseline resolving 16 of the 28 compounds in the reversed-phase mode. The acetyl-β-cyclodextrin and 2,3-dimethyl-β-cyclodextrin also showed enantioselectivity for a large number (18 and 17, respectively) of dihydrofurocoumarins in the reversed-phase mode. The native cyclodextrins are ineffective and the aromatic derivatized β-cyclodextrins are only marginally effective at separating the furocoumarin enantiomers in the reversed-phase mode. The polar organic mode and the normal-phase mode have also been evaluated with these CSPs, but no enantioseparations were observed.
Keywords :
Cyclodextrins , Dihydrofurocoumarins
Journal title :
Journal of Chromatography A
Serial Year :
2003
Journal title :
Journal of Chromatography A
Record number :
1519472
Link To Document :
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