Chankvetadze B, Pintore G, Burjanadze N, Bergenthal D, Strickmann D, Cerri R, Blaschke G
Institute of Pharmaceutical Chemistry, University of Münster, Germany.
Electrophoresis. 1998 Sep;19(12):2101-8. doi: 10.1002/elps.1150191210.
Markedly different chiral separation abilities were observed for native beta-cyclodextrin (beta-CD), carboxymethyl-beta-CD (CM-beta-CD) and heptakis (2,3,6-tri-O-methyl)-beta-CD (TM-beta-CD) towards the enantiomers of (+/-)-chlorpheniramine ((+/-)-CHL) in capillary electrophoresis (CE). Native beta-CD afforded almost baseline enantioseparation at a concentration of 18 mg/mL, whereas only 1 mg/mL solution of CM-beta-CD was required for adequate enantioseparation. TM-beta-CD allowed the nearly baseline enantioseparation only at a concentration as high as 80 mg/mL. Moreover, the migration order of (+/-)-CHL in the presence of TM-beta-CD was opposite to that with beta-CD and CM-beta-CD. 1H and 13C-NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS) have been used in order to obtain preliminary information about the stoichiometry and the binding constants in the intermolecular diastereomeric complexes of (+/-)-CHL with these CDs.
在毛细管电泳（CE）中，观察到天然β-环糊精（β-CD）、羧甲基-β-环糊精（CM-β-CD）和七（2,3,6-三-O-甲基）-β-环糊精（TM-β-CD）对（±）-氯苯那敏（（±）-CHL）对映体具有明显不同的手性分离能力。天然β-CD在浓度为18mg/mL时几乎实现了基线对映体分离，而CM-β-CD仅需1mg/mL的溶液就能实现充分的对映体分离。TM-β-CD仅在高达80mg/mL的浓度下才能实现近乎基线的对映体分离。此外，在TM-β-CD存在下（±）-CHL的迁移顺序与β-CD和CM-β-CD存在时相反。已使用1H和13C核磁共振光谱以及电喷雾电离质谱（ESI-MS）来获取有关（±）-CHL与这些环糊精分子间非对映异构体络合物的化学计量和结合常数的初步信息。
