Combined approach using capillary electrophoresis and NMR spectroscopy for an understanding of enantioselective recognition mechanisms by cyclodextrins

被引:147
作者
Chankvetadze, B [1 ]
机构
[1] Tbilisi State Univ, Sch Chem, Mol Recognit & Separat Sci Lab, GE-380028 Tbilisi, Georgia
关键词
D O I
10.1039/b111412n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This tutorial review describes the contribution of chiral capillary electrophoresis in combination with other instrumental techniques, especially nuclear magnetic resonance spectroscopy, to a better understanding of the chiral recognition mechanisms by cyclodextrins. Aspects such as affinity pattern of enantiomers towards various cyclodextrins as well as the stoichiometry of the resulting complexes, the equilibrium constants and the structure of complexes are addressed. In addition to the aforementioned techniques, the usefulness of complementary instrumental and molecular modeling techniques for an understanding of the chiral recognition mechanisms of cyclodextrins is also illustrated.
引用
收藏
页码:337 / 347
页数:11
相关论文
共 74 条
[1]   SEPARATION OF STEREOISOMERS OF AMINOGLUTETHIMIDE USING 3 CAPILLARY ELECTROPHORETIC TECHNIQUES [J].
ANIGBOGU, VC ;
COPPER, CL ;
SEPANIAK, MJ .
JOURNAL OF CHROMATOGRAPHY A, 1995, 705 (02) :343-349
[2]   SEPARATION OF DRUG STEREOISOMERS BY THE FORMATION OF BETA-CYCLODEXTRIN INCLUSION COMPLEXES [J].
ARMSTRONG, DW ;
WARD, TJ ;
ARMSTRONG, RD ;
BEESLEY, TE .
SCIENCE, 1986, 232 (4754) :1132-1135
[3]   Effect of beta-cyclodextrin acetylation on the resolution of phenethylamines with capillary electrophoresis and nuclear magnetic resonance spectroscopy [J].
Branch, SK ;
Holzgrabe, U ;
Jefferies, TM ;
Mallwitz, H ;
Oxley, FJR .
JOURNAL OF CHROMATOGRAPHY A, 1997, 758 (02) :277-292
[4]   CHIRAL DISCRIMINATION OF PHENETHYLAMINES WITH BETA-CYCLODEXTRIN AND HEPTAKIS(2,3-DI-O-ACETYL)BETA-CYCLODEXTRIN BY CAPILLARY ELECTROPHORESIS AND NMR-SPECTROSCOPY [J].
BRANCH, SK ;
HOLZGRABE, U ;
JEFFERIES, TM ;
MALLWITZ, H ;
MATCHETT, MW .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 1994, 12 (12) :1507-1517
[5]   APPLICATION OF CYCLODEXTRINS TO CHIRAL ANALYSIS BY H-1-NMR SPECTROSCOPY [J].
CASY, AF ;
MERCER, AD .
MAGNETIC RESONANCE IN CHEMISTRY, 1988, 26 (09) :765-774
[6]   Charged cyclodextrin derivatives as chiral selectors in capillary electrophoresis [J].
Chankvetadze, B ;
Endresz, G ;
Blaschke, G .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :141-&
[7]   Separation selectivity in chiral capillary electrophoresis with charged selectors [J].
Chankvetadze, B .
JOURNAL OF CHROMATOGRAPHY A, 1997, 792 (1-2) :269-295
[8]   Enantioseparations in capillary electromigration techniques: recent developments and future trends [J].
Chankvetadze, B ;
Blaschke, G .
JOURNAL OF CHROMATOGRAPHY A, 2001, 906 (1-2) :309-363
[9]   Separation of brompheniramine enantiomers by capillary electrophoresis and study of chiral recognition mechanisms of cyclodextrins using NMR-spectroscopy, UV spectrometry, electrospray ionization mass spectrometry and X-ray crystallography [J].
Chankvetadze, B ;
Burjanadze, N ;
Pintore, G ;
Bergenthal, D ;
Bergander, K ;
Mühlenbrock, C ;
Breitkreuz, J ;
Blaschke, G .
JOURNAL OF CHROMATOGRAPHY A, 2000, 875 (1-2) :471-484
[10]   Comparative enantioseparations with native β-cyclodextrin, randomly acetylated β-cyclodextrin and heptakis-(2,3-di-O-acetyl)-β-cyclodextrin in capillary electrophoresis [J].
Chankvetadze, B ;
Lomsadze, K ;
Burjanadze, N ;
Breitkreutz, J ;
Pintore, G ;
Chessa, M ;
Bergander, K ;
Blaschke, G .
ELECTROPHORESIS, 2003, 24 (06) :1083-1091