以羟丙基-<i>β</i>-环糊精为手性添加剂拆分2-取代芳基丙酸:取代基对手性识别的影响（英文）

引用本文: 王小平, 鲁梦霞, 步知思, 吕力琼, 童胜强. 以羟丙基-β-环糊精为手性添加剂拆分2-取代芳基丙酸:取代基对手性识别的影响（英文）[J]. 色谱, 2017, 35(5): 544-550. doi: 10.3724/SP.J.1123.2016.12020 shu

Citation: WANG Xiaoping, LU Mengxia, BU Zhisi, LÜ Liqiong, TONG Shengqiang. Enantioseparation of 2-(substituted phenyl) propanoic acids with hydroxypropyl-β-cyclodextrin as a chiral additive:investigation of substituent influence on enantiorecognition[J]. Chinese Journal of Chromatography, 2017, 35(5): 544-550. doi: 10.3724/SP.J.1123.2016.12020 shu

以羟丙基-β-环糊精为手性添加剂拆分2-取代芳基丙酸:取代基对手性识别的影响（英文）

浙江工业大学药学院, 浙江杭州 310032
基金项目:
Project of Department of Education of Zhejiang Province,China (No.pd2013031).

摘要: 以羟丙基-β-环糊精为手性添加剂，采用反相高效液相色谱法对2-取代芳基丙酸类物质进行了手性拆分。考察了流动相的组成，包括缓冲溶液、有机改性剂以及添加剂的浓度等。缓冲溶液的pH值、有机改性剂的种类与浓度，以及添加剂的浓度对色谱峰的保留时间和分离度均有较大的影响。以YMC ODS-C₁₈（150 mm×4.6 mm，5μm）为色谱柱，乙腈-0.10 mol/L磷酸盐缓冲液（pH 3.3，含25 mmol/L添加剂）为流动相，测定了各2-取代芳基丙酸与羟丙基-β-环糊精的包结常数，考察了羟丙基-β-环糊精对各物质的包结形式。实验结果表明，羟丙基-β-环糊精与各对映体均以1：1的形式包结，同时发现推电子取代基更有利于羟丙基-β-环糊精的包结行为，为羟丙基-β-环糊精对手性拆分的影响提供了一个有利的参考因素。

关键词:

English

Enantioseparation of 2-(substituted phenyl) propanoic acids with hydroxypropyl-β-cyclodextrin as a chiral additive:investigation of substituent influence on enantiorecognition

College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, China
Received Date: 09 December 2016
Fund Project:
Project of Department of Education of Zhejiang Province,China (No.pd2013031).

Abstract: 2-(Substituted phenyl) propanoic acids were successfully enantioseparated by reversed-phase high-performance liquid chromatography with hydroxypropyl-β-cyclodextrin as a mobile phase additive.The effect of the mobile phase composition,including the aqueous buffer,the organic modifier,and the concentration of the additive,were investigated.The aqueous buffer pH,the type and percentage of the organic modifier,and the additive concentration had a great influence on the retention time and peak resolution.Enantioseparations were achieved on an YMC ODS-C₁₈(150 mm×4.6 mm,5 μm) column.The mobile phase was composed of acetoni-trile and 0.10 mol/L of phosphate buffer at pH 3.3 containing 25 mmol/L of the hydroxypropyl-β-cyclodextrin additive.The binding constants of the inclusion complex between each of the 2-(substituted phenyl) propanoic acids and hydroxypropyl-β-cyclodextrin were determined,and the formation of the inclusion complex was investigated.The results showed that the stoichiometries for all of the inclusion complexes between hydroxypropyl-β-cyclodextrin and enantiomers were 1:1.It was found that the electron-donating group of the enantiomer was advantageous for enantiorecognition by hydroxypropyl-β-cyclodextrin.The results provide a useful reference for the influence of the enantiorecognitionfactors produced by hydroxypropyl-β-cyclodextrin.Key words:enantioseparation;high-performance liquid chromatography (HPLC);2-(substituted phenyl) pro-panoic acids;hydroxypropyl-β-cyclodextrin

Key words:

enantioseparation
/ high-performance liquid chromatography (HPLC)
/ 2-(substituted phenyl) pro- panoic acids
/ hydroxypropyl-β-cyclodextrin

1. [1] Evans A M. Eur J Clin Pharmacol, 1992, 42:237
2. [2] Wang R Q, Ong T T, Tang W H, et al. Anal Chim Acta, 2012, 718:121
3. [3] Zhong Q Q, He L F, Beesley T E, et al. J Chromatogr A, 2006, 1115:19
4. [4] Wang Y, Ong T T, Li L S, et al. J Chromatogr A, 2009, 1216:2388
5. [5] Overbeke A V, Baeyens W, Dewaele C. Anal Chim Acta, 1996, 321:245
6. [6] Luo A, Wan Q, Fan H J, et al. Chinese Journal of Chroma- tography, 2014, 32(9):1013
7. [7] Wang M. Chinese Journal of Chromatography, 2014, 32(2):198
8. [8] Zheng Y, Yan J Z, Tong S Q, et al. Chinese Journal of Phar- maceutical Analysis, 2013, 33(4):827
9. [9] Ye J C, Yu W Y, Chen G S, et al. Biomed Chromatogr, 2010, 24:799
10. [10] Tong S Q, Wang X P, Lu M X, et al. J Sep Sci, 2016, 39:1567
11. [11] Tong S Q, Guan Y X, Yan J Z, et al. J Chromatogr A, 2011, 1218:5434
12. [12] Tong S Q, Zheng Y, Yan J Z. J Chromatogr A, 2013, 1281:79
13. [13] Armstrong D W, Nome F, Spino L A, et al. J Am Chem Soc, 1986, 108:1418

扫一扫看文章

计量

PDF下载量: 3
文章访问数: 661
HTML全文浏览量: 55

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

以羟丙基-β-环糊精为手性添加剂拆分2-取代芳基丙酸:取代基对手性识别的影响（英文）

English

Enantioseparation of 2-(substituted phenyl) propanoic acids with hydroxypropyl-β-cyclodextrin as a chiral additive:investigation of substituent influence on enantiorecognition

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

以羟丙基-β-环糊精为手性添加剂拆分2-取代芳基丙酸:取代基对手性识别的影响（英文）

English

Enantioseparation of 2-(substituted phenyl) propanoic acids with hydroxypropyl-β-cyclodextrin as a chiral additive:investigation of substituent influence on enantiorecognition

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs