title: Influence of the linking spacer length and type on the enantioseparation ability of β-cyclodextrin functionalized monoliths.
abstract: In order to investigate the effect of the linking spacer on the enantioseparation ability of β-cyclodextrin (β-CD) functionalized polymeric monoliths, three β-CD-functionalized organic polymeric monoliths with different spacer lengths were prepared by using three amino-β-CDs, i.e. mono-6-amino-6-deoxy-β-CD, mono-6-ethylenediamine-6-deoxy-β-CD, mono-6-hexamethylenediamine-6-deoxy-β-CD, as starting materials. These amino-β-CDs reacted with glycidyl methacrylate to produce functional monomers which were then copolymerized with ethylene dimethacrylate. The enantioseparation ability of the three monoliths was evaluated using 14 chiral acidic compounds, including mandelic acid derivatives, nonsteroidal anti-inflammatory drugs, N-derivatized amino acids, and chiral herbicides under optimum chromatographic conditions. Notably, the poly(GMA-NH2-β-CD-co-EDMA) column provides higher enantioresolution and enantioselectivity than the poly(GMA-EDA-β-CD-co-EDMA) and poly(GMA-HDA-β-CD-co-EDMA) columns for most tested chiral analytes. Furthermore, the enantioseparation performance of triazole-linker containing monoliths was compared to that of ethylenediamine-linker containing monoliths. The results indicate that the enantioselectivity of β-CD monolithic columns is strongly related to the length and type of spacer tethering β-CD to the polymeric support.
authors.affiliation: Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China.
authors.forename: Jialiang
authors.initials: J
authors.lastname: Guo
authors.affiliation: Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China.
authors.forename: Yuan
authors.initials: Y
authors.lastname: Xiao
authors.affiliation: Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China.
authors.forename: Yuanjing
authors.initials: Y
authors.lastname: Lin
authors.affiliation: Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China.
authors.forename: Qiaoxuan
authors.initials: Q
authors.lastname: Zhang
authors.affiliation: Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China.
authors.forename: Yiqun
authors.initials: Y
authors.lastname: Chang
authors.affiliation: Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China; Laboratory of Analytical Pharmaceutical Chemistry, Department of Pharmaceutical Sciences, University of Liege, CHU B36, B-4000 Liege, Belgium.
authors.forename: Jacques
authors.initials: J
authors.lastname: Crommen
authors.affiliation: Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China. Electronic address: jzjjackson@hotmail.com.
authors.forename: Zhengjin
authors.initials: Z
authors.lastname: Jiang
mesh_terms: D000586:Amination; D000596:Amino Acids / Q000737:chemistry; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation*; D004852:Epoxy Compounds / Q000737:chemistry*; D005029:Ethylenediamines / Q000737:chemistry; D008333:Mandelic Acids / Q000737:chemistry; D008689:Methacrylates / Q000737:chemistry*; D008768:Methylmethacrylates / Q000737:chemistry; D058105:Polymerization; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D000894:Anti-Inflammatory Agents, Non-Steroidal; D004852:Epoxy Compounds; D005029:Ethylenediamines; D008333:Mandelic Acids; D008689:Methacrylates; D008768:Methylmethacrylates; D014230:Triazoles; D047392:beta-Cyclodextrins; C020347:GMA-EDMA; C031234:ethylenediamine; C004919:ethylene dimethacrylate; C037938:mandelic acid; C007870:glycidyl methacrylate
keywords: Enantioseparation; Linking spacer; Monolithic columns; β-cyclodextrins