title: Comparative HPLC enantioseparation on substituted phenylcarbamoylated cyclodextrin chiral stationary phases and mobile phase effects.
abstract: Two new cyclodextrin-derived chiral stationary phases with multiple urea linkages were prepared through the Staudinger reactions between aminopropyl silica gel and cyclodextrin derivatives, namely, heptakis(6-azido-6-deoxy-2,3-di-O-3,5-dimethylphenylcarbamoylated)-β-cyclodextrin and heptakis(6-azido-6-deoxy-2,3-di-O-3,5-dichlorophenylcarbamoylated)-β-cyclodextrin, respectively. HPLC separation behaviors toward 46 chiral analytes have been investigated under multimodal elution. They exhibited good separation performances for these analytes and also showed some complimentary enantioselectivity to each other, due to different electron-donating (methyl)/withdrawing (chlorine) groups in the phenylcarbamate moieties. Among these analytes, aromatic alcohols and N-(2,4-dinitrophenyl)-derived carboxylic acids were better resolved on the π-basic chiral stationary phase than the π-acidic. The proton pump inhibitors, the 5-hydroxytryptamine receptor antagonists, and the analytes with carbonyl groups easily formed stereoselective interactions with the π-acidic chiral stationary phase, further leading to better enantioseparation. Elution order reversal for palonosetron and N-(2,4-dinitrophenyl) glutamine was observed in three chiral stationary phases, probably induced by the difference of phenylcarbamate groups. Moreover, mobile phase effects on retention behaviors of analytes have been studied in detail.
authors.affiliation: School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China.
authors.forename: Chun
authors.initials: C
authors.lastname: Lin
authors.affiliation: School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China. Electronic address: fanj@scnu.edu.cn.
authors.forename: Jun
authors.initials: J
authors.lastname: Fan
authors.affiliation: School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China.
authors.forename: Wen-na
authors.initials: WN
authors.lastname: Liu
authors.affiliation: Guangzhou Research and Creativity Biotechnology Co. Ltd, Guangzhou 510663, China.
authors.forename: Yi
authors.initials: Y
authors.lastname: Tan
authors.affiliation: School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China; Guangzhou Research and Creativity Biotechnology Co. Ltd, Guangzhou 510663, China. Electronic address: wgzhang@scnu.edu.cn.
authors.forename: Wei-guang
authors.initials: WG
authors.lastname: Zhang
mesh_terms: D000438:Alcohols / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003505:Cyclodextrins / Q000737:chemistry*; D048448:Phenylcarbamates / Q000737:chemistry*; D011985:Receptors, Serotonin / Q000378:metabolism; D012702:Serotonin Antagonists / Q000737:chemistry; D012822:Silicon Dioxide / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D003505:Cyclodextrins; D048448:Phenylcarbamates; D011985:Receptors, Serotonin; D012702:Serotonin Antagonists; C021611:aminopropyl silica gel; D012822:Silicon Dioxide
keywords: Complimentary behavior; Cyclodextrin chiral stationary phase; Enantioseparation; Mobile phase effects; Multiple urea linkage