Effect of the crosslinker type on the enantioseparation performance of β-cyclodextrin functionalized monoliths prepared by the one-pot approach.
Low column efficiency for enantioseparations in capillary liquid chromatography (CLC) is a major problem commonly encountered with β-cyclodextrin (β-CD) functionalized polymer-based monoliths. In order to investigate the effect of the crosslinker type on enantioseparation performance, three commonly used crosslinkers, i.e. 1,4-bis(acryloyl)piperazine (PDA), ethylene dimethacrylate (EDMA) and N,N-methylenebisacrylamide (MBA), were copolymerized using the one-pot approach with glycidyl methacrylate-mono-6-amino-6-deoxy-β-CD (GMA-NH2-β-CD) as functional monomer. The three monolithic columns, including poly(GMA-NH2-β-CD-co-PDA) and poly(GMA-NH2-β-CD-co-MBA), as well as the previously reported column poly(GMA-NH2-β-CD-co-EDMA) were systematically compared with respect to morphology, permeability, β-CD density, retention mechanism and efficiency. The enantioseparation ability of each column was evaluated using 14 chiral compounds, including mandelic acid derivatives, profens, N-derivatized amino acids, and herbicides, as test substances. The β-CD-functionalized monolith with MBA as crosslinker was found to exhibit higher polarity, higher column efficiency and better enantioseparation performance than those with PDA or EDMA as crosslinker.
Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China.
Jialiang
J
Guo
Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China.
Yuan
Y
Xiao
Department of Pharmacy and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine & New Drug Research, Jinan University, Guangzhou 510632, China.
Yuanjing
Y
Lin
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.
Jacques
J
Crommen
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.
Zhengjin
Z
Jiang
D000178:Acrylamides / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods; D003432:Cross-Linking Reagents / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D006540:Herbicides / Q000737:chemistry / Q000302:isolation & purification; D008333:Mandelic Acids / Q000737:chemistry / Q000302:isolation & purification; D008689:Methacrylates / Q000737:chemistry; D010539:Permeability; D010666:Phenylpropionates / Q000737:chemistry / Q000302:isolation & purification; D058105:Polymerization; D047392:beta-Cyclodextrins / Q000737:chemistry*
D000178:Acrylamides; D000596:Amino Acids; D003432:Cross-Linking Reagents; D004852:Epoxy Compounds; D006540:Herbicides; D008333:Mandelic Acids; D008689:Methacrylates; D010666:Phenylpropionates; D047392:beta-Cyclodextrins; C004919:ethylene dimethacrylate; C021221:N,N'-methylenebisacrylamide; C031215:betadex; C007870:glycidyl methacrylate
Crosslinker; Cyclodextrin; Enantioseparation; Monolithic column