Dual chiral recognition system involving cyclodextrin derivatives in capillary electrophoresis II. Enhancement of enantioselectivity.
The enantiomer separation of hexobarbital was investigated by open tubular electrochromatography (OTEC) using the chiral stationary phase (CSP) CHIRASIL-DEX (a permethylated beta-cyclodextrin covalently linked to a dimethylpolysiloxane) and by cyclodextrin-electrokinetic chromatogaphy (CD-EKC) using anionic beta-cyclodextrin-sulfo-n-propyl ether (SPE-beta-CD) and cationic beta-cyclodextrin-2-hydroxy-3-trimethylammoniumpropyl ether chloride (HTAP-beta-CD) added to the running buffer. By employing two chiral selectors, the enantiomer separation of hexobarbital was then studied simultaneously by OTEC with CHIRASIL-DEX and by CD-EKC with either SPE-beta-CD or HTAP-beta-CD in the dual chiral recognition mode. In conjunction with CHIRASIL-DEX, anionic SPE-beta-CD decreased the chiral separation factor alpha due to compensation of enantioselectivity whereas the cationic additive HTAP-beta-CD increased the chiral separation factor alpha due to enhancement of enantioselectivity. It is concluded that CHIRASIL-DEX imparts an opposite enantioselectivity to the enantiomers of hexobarbital as compared to the charged CDs SPE-beta-CD and HTAP-beta-CD. Unusual peak broadening phenomena are observed in the dual chiral recognition system comprised of CHIRASIL-DEX and HTAP-beta-CD. The possible consequences of accidental dual chiral recognition systems caused by wall stacking effects of the mobile phase additives onto the inner surface of the capillary column are discussed.
Jakubetz
H
H
Institut für Organische Chemie, Universität Tübingen, Germany.
Juza
M
M
Schurig
V
V
D000180:Acrylic Resins; D002240:Carbohydrate Sequence; D003505:Cyclodextrins / Q000737:chemistry; D019075:Electrophoresis, Capillary / Q000379:methods*; D006591:Hexobarbital / Q000302:isolation & purification*; D006993:Hypnotics and Sedatives; D008969:Molecular Sequence Data; D015394:Molecular Structure; D011412:Propanolamines / Q000737:chemistry; D012822:Silicon Dioxide; D013451:Sulfonic Acids / Q000737:chemistry; D047392:beta-Cyclodextrins; D000099166:Polyacrylamides
D000180:Acrylic Resins; D003505:Cyclodextrins; D006591:Hexobarbital; D006993:Hypnotics and Sedatives; D011412:Propanolamines; D012822:Silicon Dioxide; D013451:Sulfonic Acids; D047392:beta-Cyclodextrins; D000099166:Polyacrylamides; C113663:beta-cyclodextrin-2-hydroxy-3-trimethylammoniumpropyl ether chloride; C113664:beta-cyclodextrin-sulfo-n-propyl ether