Comparative enantioseparations with native beta-cyclodextrin, randomly acetylated beta-cyclodextrin and heptakis-(2,3-di-O-acetyl)-beta-cyclodextrin in capillary electrophoresis.
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-CD (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-CD and HDA-beta-CD.
Chankvetadze
Bezhan
B
Molecular Recognition and Separation Science Laboratory, School of Chemistry, Tbilisi State University, Tbilisi, Georgia. bchankvetadze@yahoo.com
Lomsadze
Ketevan
K
Burjanadze
Naira
N
Breitkreutz
Joerg
J
Pintore
Giorgio
G
Chessa
Mario
M
Bergander
Klaus
K
Blaschke
Gottfried
G
D000107:Acetylation; D002846:Chromatography, Affinity; D003505:Cyclodextrins / Q000737:chemistry* / Q000302:isolation & purification*; D019075:Electrophoresis, Capillary / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D012996:Solutions / Q000737:chemistry; D047392:beta-Cyclodextrins
D003505:Cyclodextrins; D012996:Solutions; D047392:beta-Cyclodextrins; C092855:heptakis(2,3-di-O-acetyl)beta-cyclodextrin; C031215:betadex