title: Novel cyclodextrin chiral stationary phases for high performance liquid chromatography enantioseparation: effect of cyclodextrin type.
abstract: Three novel chiral stationary phases (CSPs) were prepared by regioselective chemical immobilization of mono(6(A)-N-allylamino-6(A)-deoxy)perphenylcarbamoylated (PICD) α-, β-, and γ-cyclodextrins (CDs) onto silica support via hydrosilylation. Their enantioseparation properties in high performance liquid chromatography (HPLC) were evaluated with a large spectrum of racemates including flavanone compounds, β-adrenergic blockers, amines and non-protolytic compounds. The effect of CD's cavity size on enantioseparation abilities was studied and discussed. The results indicated that CD's surface loading at silica support played an important role in the enantioseparation on these CSPs under normal-phase conditions while inclusion phenomena contributed the major driving force under reverse-phase conditions. As expected, α-PICD demonstrated the best resolutions towards flavonone and most aromatic alcohols under normal-phase conditions with the highest surface loading; while Fujimura's competitive inclusion model can be applied to explain the better enantioseparations towards β-adrenergic blockers, amines and non-protolytic compounds with α- and β-PICD CSPs. γ-PICD CSP showed superior enantioseparation ability for sterically encumbered analytes like flavanone compounds under both normal-phase and reversed phase conditions.
authors.affiliation: Division of Chemical and Biomolecular Engineering, College of Engineering, Nanyang Technological University, 16 Nanyang Drive, Singapore 637722, Singapore.
authors.forename: Xianghua
authors.initials: X
authors.lastname: Lai
authors.forename: Weihua
authors.initials: W
authors.lastname: Tang
authors.forename: Siu-Choon
authors.initials: SC
authors.lastname: Ng
mesh_terms: D000327:Adsorption; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D003505:Cyclodextrins / Q000737:chemistry*; D004364:Pharmaceutical Preparations / Q000032:analysis*; D013237:Stereoisomerism
chemical_list: D003505:Cyclodextrins; D004364:Pharmaceutical Preparations