title: A novel hydroquinidine imprinted microsphere using a chirality-matching N-acryloyl-L-phenylalanine monomer for recognition of cinchona alkaloids.
abstract: Using a combination of molecular imprinting technology and traditional chiral stationary phases, the synergistic effect between chiral monomer and chiral cavity of molecularly imprinted polymers in stereoselective recognition was investigated. We designed and synthesized an amino acid derivative to be used as a novel chiral functional monomer. Monodisperse molecularly imprinted core-shell microspheres using surface imprinting method on silica gel were prepared with hydroquinidine as the pseudo-template molecule for the resolution of cinchona alkaloids. The results showed a significant synergistic effect in stereoselective recognition, confirming our initial hypothesis. Furthermore, our computational simulation and experiments intensively support the hypothetical chiral recognition mechanism for the imprinted microspheres.
authors.affiliation: Department of Chemistry, South China Normal University, Guangzhou 510006, China.
authors.forename: Qi
authors.initials: Q
authors.lastname: Zhou
authors.forename: Jing
authors.initials: J
authors.lastname: He
authors.forename: Youwen
authors.initials: Y
authors.lastname: Tang
authors.forename: Zhiguang
authors.initials: Z
authors.lastname: Xu
authors.forename: He
authors.initials: H
authors.lastname: Li
authors.forename: Chengcheng
authors.initials: C
authors.lastname: Kang
authors.forename: Jiabing
authors.initials: J
authors.lastname: Jiang
mesh_terms: D000179:Acrylates / Q000737:chemistry; D000327:Adsorption; D002851:Chromatography, High Pressure Liquid; D002930:Cinchona Alkaloids / Q000032:analysis*; D003198:Computer Simulation; D005021:Ethylamines / Q000737:chemistry; D000432:Methanol; D008863:Microspheres; D054802:Molecular Imprinting / Q000379:methods*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D011802:Quinidine / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000179:Acrylates; D002930:Cinchona Alkaloids; D005021:Ethylamines; D010649:Phenylalanine; C014486:hydroquinidine; D011802:Quinidine; C016162:triethylamine; D000432:Methanol