Chiral discrimination of phenethylamines with beta-cyclodextrin and heptakis(2,3-di-O-acetyl)beta-cyclodextrin by capillary electrophoresis and NMR spectroscopy.
The resolution of nine sympathomimetic phenethylamine racemates by beta-cyclodextrin and heptakis(2,3-di-O-acetyl)beta-cyclodextrin has been investigated by capillary electrophoresis and 1H NMR spectroscopy. The NMR and capillary electrophoresis results showed that beta-cyclodextrin probably formed stronger complexes with the amines than did heptakis(2,3-di-O-acetyl)beta-cyclodextrin but was a poorer chiral discrimination agent in both techniques. The addition of heptakis(2,3-di-O-acetyl)beta-cyclodextrin to the capillary electrophoresis buffer gave baseline resolution of enantiomer peaks for seven of the compounds studied while beta-cyclodextrin resolved only three of the racemates.
Branch
S K
SK
School of Pharmacy and Pharmacology, University of Bath, Claverton Down, UK.
Holzgrabe
U
U
Jefferies
T M
TM
Mallwitz
H
H
Matchett
M W
MW
D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry*; D004586:Electrophoresis / Q000379:methods; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D010627:Phenethylamines / Q000737:chemistry*; D013237:Stereoisomerism; D047392:beta-Cyclodextrins
D003505:Cyclodextrins; D010627:Phenethylamines; D047392:beta-Cyclodextrins; C092855:heptakis(2,3-di-O-acetyl)beta-cyclodextrin; C031215:betadex