有机化学 ›› 2015, Vol. 35 ›› Issue (1): 217-222.DOI: 10.6023/cjoc201408011 上一篇    下一篇

研究简报

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   

  1. 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 出版日期:2015-01-25 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   

  1. Faculty of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500
  • Received:2014-08-11 Revised:2014-09-23 Online:2015-01-25 Published:2014-10-09
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21275126, 21127012).

R-联萘酚为原料, 利用铃木反应改进合成了已有文献报道的R-(3,3'-二苯基-1,1'-二萘基)-20-冠-6, 并将其涂敷于C18硅胶(平均粒径5 μm, 孔径120 Å)上制成了可用于高效液相色谱手性拆分的R-(3,3'-二苯基-1,1'-二萘基)-20-冠-6冠醚固定相(CSP). 在以pH=2的高氯酸溶液为流动相, 流速为0.1 mL·min-1, 柱温为25 ℃的条件下, 研究了R-(3,3'-二苯基-1,1'-二萘基)-20-冠-6冠醚固定相(CSP)对13种α-氨基酸对映体的拆分能力, 并将其拆分结果与商品CR(+)柱进行了对比. 实验结果表明在此色谱条件下, 有11种α-氨基酸对映体(苯甘氨酸、对羟基苯甘氨酸、蛋氨酸、酪氨酸、色氨酸、缬氨酸、亮氨酸、异亮氨酸、苯丙氨酸、谷氨酸、天冬氨酸)能得到不同程度的拆分, 并且对其中6种α-氨基酸对映体的拆分效果要好于商品CR(+)柱. 研究表明此冠醚手性固定相对α-氨基酸对映体有很好的手性识别能力, 在对α-氨基酸对映体的拆分上能与商品CR(+)柱相媲美.

关键词: α-氨基酸对映体, 冠醚, 手性固定相, 手性识别, 高效液相色谱

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