Comparative enantioseparations with native β-cyclodextrin, randomly acetylated β-cyclodextrin and heptakis-(2,3-di-O-acetyl)-β-cyclodextrin in capillary electrophoresis

被引:39
作者
Chankvetadze, B
Lomsadze, K
Burjanadze, N
Breitkreutz, J
Pintore, G
Chessa, M
Bergander, K
Blaschke, G
机构
[1] Tbilisi State Univ, Sch Chem, Mol Recognit & Separat Sci Lab, GE-380086 Tbilisi, Georgia
[2] Univ Munster, Inst Pharmaceut & Med Chem, D-4400 Munster, Germany
[3] Univ Munster, Inst Pharmaceut Technol & Biopharmaceut, D-4400 Munster, Germany
[4] Univ Sassari, Fac Pharm, Dipartimento Farmacochimicotossicol, I-07100 Sassari, Italy
[5] Univ Munster, Inst Organ Chem, D-4400 Munster, Germany
关键词
capillary electrophoresis; cycloclextrin; enantioseparation; enantiomer migration order; rotating frame nuclear Overhauser effect spectroscopy;
D O I
10.1002/elps.200390126
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
Comparative enantioseparations were performed with three neutral cyclodextrins (CDs) in capillary electrophoresis (CE). In particular, native beta-CD was compared with single component heptakis(2,3-di-O-acetyl)-beta-CID (HDA-beta-CD) and randomly acetylated beta-CD (Ac-beta-CD) with the emphasis on the enantiomer migration order. The opposite affinity of the enantiomers of several chiral analytes was observed towards native beta-CD and its acetylated derivatives. The enantiomer affinity pattern of some chiral analytes was also opposite towards the two acetylated derivatives of beta-CD. In the case of the chiral drug clenbuterol (CL) an attempt was made to evaluate the possible structural reasons of the affinity reversal using one- and two-dimensional as well as transverse rotating frame nuclear Overhauser effect spectroscopy (ROESY). Significant differences were observed between the structure of the CL complexes with beta-CID and HDA-beta-CD.
引用
收藏
页码:1083 / 1091
页数:9
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