title: Improvement of chiral stationary phases based on cinchona alkaloids bonded to crown ethers by chiral modification.
abstract: To improve the chiral recognition capability of a cinchona alkaloid crown ether chiral stationary phase, the crown ether moiety was modified by the chiral group of (1S, 2S)-2-aminocyclohexyl phenylcarbamate. Both quinine and quinidine-based stationary phases were evaluated by chiral acids, chiral primary amines and amino acids. The quinine/quinidine and crown ether provided ion-exchange sites and complex interaction site for carboxyl group and primary amine group in amino acids, respectively, which were necessary for the chiral discrimination of amino acid enantiomers. The introduction of the chiral group greatly improved the chiral recognition for chiral primary amines. The structure of crown ether moiety was proved to play a dominant role in the chiral recognitions for chiral primary amines and amino acids.
authors.affiliation: Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, China.
authors.forename: Jianchao
authors.initials: J
authors.lastname: Zhao
authors.affiliation: Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, China.
authors.forename: Haixia
authors.initials: H
authors.lastname: Wu
authors.affiliation: Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, China.
authors.forename: Dongqiang
authors.initials: D
authors.lastname: Wang
authors.affiliation: Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, China.
authors.forename: Haibo
authors.initials: H
authors.lastname: Wu
authors.affiliation: Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, China.
authors.forename: Lingping
authors.initials: L
authors.lastname: Cheng
authors.affiliation: Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Jin
authors.affiliation: Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, China.
authors.forename: Yanxiong
authors.initials: Y
authors.lastname: Ke
authors.affiliation: Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, China.|Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China.
authors.forename: Xinmiao
authors.initials: X
authors.lastname: Liang
keywords: Amino acids; Chiral selectors; Cinchona alkaloids; Crown ethers; Enantioseparation