Wang Dongqiang, Zhao Jianchao, Wu Haixia, Wu Haibo, Cai Jianfeng, Ke Yanxiong, Liang Xinmiao
Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, China.
J Sep Sci. 2015 Jan;38(2):205-10. doi: 10.1002/jssc.201400977. Epub 2014 Dec 4.
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, NH4Cl, 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.
奎宁的C9位被间位或对位取代的苯并-18-冠-6修饰，并通过自由基硫醇-烯加成反应固定在3-巯基丙基修饰的硅胶上。这两种手性固定相通过手性酸、氨基酸和手性伯胺进行评价。奎宁阴离子交换剂上的冠醚部分为伯氨基提供了一个配体交换位点，这对含伯胺基团的手性化合物的保留和对映选择性起着重要作用。这两种固定相对某些氨基酸表现出良好的选择性。通过向流动相中添加LiCl、NH4Cl、NaCl和KCl等无机盐，研究了冠醚与质子化伯氨基之间的复杂相互作用。拆分结果表明，两个功能部分（奎宁和冠醚）与氨基酸之间的同时相互作用对手性分离很重要。
