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Zhao J, Wu H, Wang D, et al. Improvement of chiral stationary phases based on cinchona alkaloids bonded to crown ethers by chiral modification. J Sep Sci. 2015;38(22):3884-3890doi: 10.1002/jssc.201500834.
Zhao, J., Wu, H., Wang, D., Wu, H., Cheng, L., Jin, Y., Ke, Y., & Liang, X. (2015). Improvement of chiral stationary phases based on cinchona alkaloids bonded to crown ethers by chiral modification. Journal of separation science, 38(22), 3884-3890. https://doi.org/10.1002/jssc.201500834
Zhao, Jianchao, et al. "Improvement of chiral stationary phases based on cinchona alkaloids bonded to crown ethers by chiral modification." Journal of separation science vol. 38,22 (2015): 3884-3890. doi: https://doi.org/10.1002/jssc.201500834
Zhao J, Wu H, Wang D, Wu H, Cheng L, Jin Y, Ke Y, Liang X. Improvement of chiral stationary phases based on cinchona alkaloids bonded to crown ethers by chiral modification. J Sep Sci. 2015 Nov;38(22):3884-3890. doi: 10.1002/jssc.201500834. Epub 2015 Oct 15. PMID: 26377616.
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J Sep Sci. 2015 Nov;38(22):3884-3890. doi: 10.1002/jssc.201500834. Epub 2015 Oct 15.

Improvement of chiral stationary phases based on cinchona alkaloids bonded to crown ethers by chiral modification.

Journal of separation science

Jianchao Zhao, Haixia Wu, Dongqiang Wang, Haibo Wu, Lingping Cheng, Yu Jin, Yanxiong Ke, Xinmiao Liang

Affiliations

  1. Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, China.
  2. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China.

PMID: 26377616 DOI: 10.1002/jssc.201500834

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.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: Amino acids; Chiral selectors; Cinchona alkaloids; Crown ethers; Enantioseparation

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