Synthesis and Evaluation of Crown Ether Chiral Stationary Phase

doi:10.6023/cjoc201408011

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 217-222.DOI: 10.6023/cjoc201408011 Previous Articles Next Articles

Notes

冠醚手性固定相的合成及其性能评价

路振宇, 伍鹏, 字敏, 杨璨瑜, 孔娇, 袁黎明

云南师范大学化学化工学院昆明 650500

收稿日期:2014-08-11 修回日期:2014-09-23 发布日期:2014-10-09
通讯作者: 袁黎明 E-mail:yuan_limingpd@126.com
基金资助:
国家自然科学基金(Nos. 21275126, 21127012)资助项目.

Synthesis and Evaluation of Crown Ether Chiral Stationary Phase

Lu Zhenyu, Wu Peng, Zi Min, Yang Canyu, Kong jiao, Yuan Liming

Faculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500

Received:2014-08-11 Revised:2014-09-23 Published:2014-10-09
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21275126, 21127012).

1. Synthesis and Evaluation of Crown Ether Chiral Stationary Phase.PDF(564KB)

Abstract

In this paper, R-(3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6 was synthesized from (R)-1,1'-bi(2-naphthol), which was coated on C¹⁸ silica gel (the average particle size is 5 μm, and aperture is 120 Å). The final product (CSP) was used as the chiral stationary phase of high performance liquid chromatography for the enantioseparation of α-amino acids. In the conditions of perchloric acid solution (pH=2) as mobile phase, flow rate of 0.1 mL·min^-1, 25 ℃, the chiral recognition ability for 13 kinds of α-amino acids enantiomer on CSP was studied, and 11 kinds of α-amino acid enantiomers (phenylglycine, hydroxyphenylglycine, methionine, tyrosine, tryptophan, valine, leucine, isoleucine, phenylalanine, glutamate, aspartate) were separated. This column offers a better enantioselectivity for six kinds of α-amino acid than that of commercial CR(+) column. The experimental results showed that CSP possesses a good enantioselectivity for α-amino acid enantiomers.

Key words: α-amino acid enantiomers, crown ethers, chiral stationary phase, chiral recognition, high performance liquid chromatography

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Lu Zhenyu, Wu Peng, Zi Min, Yang Canyu, Kong jiao, Yuan Liming. Synthesis and Evaluation of Crown Ether Chiral Stationary Phase[J]. Chin. J. Org. Chem., 2015, 35(1): 217-222.

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冠醚手性固定相的合成及其性能评价

Synthesis and Evaluation of Crown Ether Chiral Stationary Phase

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