冠醚手性固定相的合成及其性能评价
收稿日期: 2014-08-11
修回日期: 2014-09-23
网络出版日期: 2014-10-09
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
Received date: 2014-08-11
Revised date: 2014-09-23
Online published: 2014-10-09
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21275126, 21127012).
以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.
路振宇 , 伍鹏 , 字敏 , 杨璨瑜 , 孔娇 , 袁黎明 . 冠醚手性固定相的合成及其性能评价[J]. 有机化学, 2015 , 35(1) : 217 -222 . DOI: 10.6023/cjoc201408011
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.
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