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Improvement of chiral stationary phases based on cinchona alkaloids bonded to crown ethers by chiral modification
Author(s) -
Zhao Jianchao,
Wu Haixia,
Wang Dongqiang,
Wu Haibo,
Cheng Lingping,
Jin Yu,
Ke Yanxiong,
Liang Xinmiao
Publication year - 2015
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.201500834
Subject(s) - cinchona , moiety , enantiomer , chiral derivatizing agent , chemistry , crown ether , quinidine , amino acid , cinchona alkaloids , organic chemistry , ether , chiral auxiliary , stereochemistry , chiral column chromatography , enantioselective synthesis , ion , catalysis , medicine , biochemistry , pharmacology
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 (1 S , 2 S )‐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.