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Preparation and evaluation of novel chiral stationary phases based on quinine derivatives comprising crown ether moieties
Author(s) -
Wang Dongqiang,
Zhao Jianchao,
Wu Haixia,
Wu Haibo,
Cai Jianfeng,
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.201400977
Subject(s) - chemistry , crown ether , moiety , amino acid , protonation , amine gas treating , ether , chiral derivatizing agent , selectivity , organic chemistry , enantiomer , medicinal chemistry , chiral column chromatography , catalysis , ion , biochemistry
The C9‐position of quinine was modified by meta ‐ or para ‐substituted benzo‐18‐crown‐6, and immobilized on 3‐mercaptopropyl‐modified silica gel through the radical thiol‐ene addition reaction. These two chiral stationary phases were evaluated by chiral acids, amino acids, and chiral primary amines. The crown ether moiety on the quinine anion exchanger provided a ligand‐exchange site for primary amino groups, which played an important role in the retention and enantioselectivity for chiral compounds containing primary amine groups. These two stationary phases showed good selectivity for some amino acids. The complex interaction between crown ether and protonated primary amino group was investigated by the addition of inorganic salts such as LiCl, NH 4 Cl, NaCl, and KCl to the mobile phase. The resolution results showed that the simultaneous interactions between two function moieties (quinine and crown ether) and amino acids were important for the chiral separation.