Citation: WU Zhi-Hua, ZHAO Jie, LI Shen, WANG Yong. Enantioseparation Performance Tuning of Novel Cyclodextrin Chiral Separation Materials via Click Chemistry[J]. Chinese Journal of Analytical Chemistry, ;2016, 44(1): 95-102. doi: 10.11895/j.issn.0253-3820.150611 shu

Enantioseparation Performance Tuning of Novel Cyclodextrin Chiral Separation Materials via Click Chemistry

WU Zhi-Hua ¹ ,
ZHAO Jie ² ,
LI Shen ¹ ,
WANG Yong ^1,3,,

1.
¹ Department of Chemistry, School of Science Tianjin University, Tianjin 300072, China;
2.
² Institute of Agricultural Resource and Environment Tianjin Academy of Agricultural Science, Tianjin 300192, China;
3.
³ Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, China

Corresponding author: WANG Yong,
Received Date: 31 July 2015
Available Online: 13 November 2015
Fund Project: 本文系国家自然科学基金(No.21205086) (No.21205086)天津市自然科学基金(No.13JCQNJC05400) (No.13JCQNJC05400)天津大学自主创新基金(No.2015XRX-0021)资助项目 (No.2015XRX-0021)

This work fabricates four novel chiral stationary phases (CSPs) by tuning the functionality on cyclodextrin (CD) small mouth via click chemistry. Mono-6-deoxy-azido CD was anchored onto silica surface via ether linkage, followed by introducing tert-butyl, phenyl, ester and hydroxyl groups to the azido CD silica respectively. The as-prepared four novel CD CSPs were characterized by FTIR and elemental analysis. 16 enantiomer pairs including isoxazolines and dansyl amino acids could be baseline or partially separated on the current CD CSPs under reversed-phase separation mode. Ester functionalized CD CSP exhibited good chiral recognition towards isoxazolines and the resolution of 2-chlorphenyl-isoxazole(2ClPh-OPr)reached 1.62. The optimum pH for the separation of dansyl amino acids was 5.0. Among the prepared CSPs, Tert-butyl functionalized CD CSP had the best enantioseparation performance towards dansyl amino acids with most of the analytes baseline separated (R_s>1.5).
- High performance liquid chromatography,
- Cyclodextrin,
- Chiral stationary phase,
- Click chemistry
1. [1]
  1 Cavazzini A, Pasti L, Massi A, Marchetti N, Dondi F. Anal. Chim. Acta, 2011,706(2):205-222
2. [2]
  2 Kuang X, Ma Y, Su H, Zhang J, Dong Y B, Tang B. Anal. Chem., 2014,86(2):1277-1281
3. [3]
  3 Yang X C, Wong S Y, Bwambok D K, Atkinson M B J, Zhang X, White-sides G M, Myerson A S. Chem. Commun., 2014,50:7548-7551
4. [4]
  4 Fortuna A, Alves G, Falcao A. Biomed. Chromatogr., 2014,28(1):27-58
5. [5]
  5 Fernandes C, Tiritan M, Pinto M. Chromatographia, 2013,76(15):871-897
6. [6]
  6 Asman S, Mohamad S, Sarih N M. Int. J. Mol. Sci., 2015,16(2):3656-3676
7. [7]
  7 Cui H, Chen L, Dong Y L, Zhong S W, Guo D Q, Zhao H, He J, Zou H, Li X J, Yuan Z B. J. Electroanal. Chem., 2015,742:15-22
8. [8]
  8 ZHANG Yang, LI Lai-Sheng, CHENG Biao-Ping, ZHOU Ren-Dan, NIE Gui-Zhen. Chinese. J. Anal. Chem., 2014,42(3):375-383 张杨, 李来生, 程彪平, 周仁丹, 聂桂珍.分析化学,2014, 42(3):375-383
9. [9]
  9 Guitet M, Zhang P, Marcelo F, Tugny C, Jiménez-Barbero J, Buriez O, Ama-tore C, Mouriès-Mansuy V, Goddard J P, Fensterbank L, Zhang Y, Roland S, Ménand M, Sollogoub M. Angew. Chem. Int. Ed., 2013,52(28):7213-7218
10. [10]
  10 Li S, Xing P, Hou Y, Yang J, Yang X, Wang B, Hao A. J. Mol. Liq., 2013,188:74-80
11. [11]
  11 Armstrong D W, Stalcup A M, Hilton M L, Duncan Jr J D, Faulkner J R, Chang S C. Anal. Chem., 1990,62(15):1610-1615
12. [12]
  12 Armstrong D W, DeMond W. J. Chromatogr. Sci., 1984,22(9):411-415
13. [13]
  13 Hilton H L, Chang S C, Gasper M P. J. Liq. Chromatogr., 1993,16:127-147
14. [14]
  14 Muderawan I W, Ong T T, Ng S C. J. Sep. Sci., 2006,29(12):1849-1871
15. [15]
  15 Liu M, Da S L, Feng Y Q, Li L S. Anal. Chim. Acta, 2005,533(2):89-95
16. [16]
  16 Zhang Y P, Guo Z M, Ye J X, Xu Q, Liang X M, Lei A W. J. Chromatogr. A, 2008,1191(1):188-192
17. [17]
  17 Yu G Y, Guo L Z, Xie F Y, Yao B X, Zeng Q L, Weng W. Chromatographia, 2011,73(11):1049-1055
18. [18]
  18 YANG Shao-Ning, LUO Ai-Qin, HOU Ai-Jun. J. Anal. Sci., 2008,24(5):615-617 杨少宁, 罗爱芹, 候爱军.分析科学学报,2008,24(5):615-617
19. [19]
  19 Zhong Q Q, He L F, Beesley T E, Trahanovsky W S, Sun P. J. Chromatogr. A, 2006,1115(1):19-45
20. [20]
  20 Araki T, Tsunoi S, Tanaka M. Anal. Chim. Acta, 2000,410(1):37-45
21. [21]
  21 Zhou Z M, Li X, Chen X P. Anal. Chim. Acta, 2010,678(2):208-214
22. [22]
  22 Zhou Z M, Fang M, Yu C X. Anal. Chim. Acta, 2005, 539(1):23-29
23. [23]
  23 Zhao J, Lu X H, Wang Y, Tan T T Y. J. Chromatogr. A, 2014,1343:101-108
24. [24]
  24 FU Chun-Mei, SHI Hong-Yu, LI Zhang-Wan, QIAN Guang-Sheng. Chinese J. Anal. Chem., 2010,38(7):1011-1014 付春梅, 石宏宇, 李章万, 钱广生.分析化学,2010,38(7):1011-1014
25. [25]
  25 NIE Ji, LI Jian-Ping, DENG Huan, PAN Hong-Cheng. Chinese J. Anal. Chem., 2015,43(4):609-617 聂骥, 李建平, 邓欢, 潘宏程.分析化学,2015,43(4):609-617
26. [26]
  26 Gong Y, Wang Y, Zhao W T, Tang X Y. J. Chem. Res., 2013, 37(8):499-502
27. [27]
  21 Yao X B, Gong Y, Mamuti R, Xing W W, Zheng H, Tang X Y. Wang Y. RSC Adv., 2014,4(8):30492-30499
1. [1]
  Fan Wu , Wenchang Tian , Jin Liu , Qiuting Zhang , YanHui Zhong , Zian Lin . Core-Shell Structured Covalent Organic Framework-Coated Silica Microspheres as Mixed-Mode Stationary Phase for High Performance Liquid Chromatography. University Chemistry, 2024, 39(11): 319-326. doi: 10.12461/PKU.DXHX202403031
2. [2]
  Siming Bian , Sijie Luo , Junjie Ou . Application of van Deemter Equation in Instrumental Analysis Teaching: A New Type of Core-Shell Stationary Phase. University Chemistry, 2025, 40(3): 381-386. doi: 10.12461/PKU.DXHX202406087
3. [3]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
4. [4]
  Runjie Li , Hang Liu , Xisheng Wang , Wanqun Zhang , Wanqun Hu , Kaiping Yang , Qiang Zhou , Si Liu , Pingping Zhu , Wei Shao . 氨基酸的衍生及手性气相色谱分离创新实验. University Chemistry, 2025, 40(6): 286-295. doi: 10.12461/PKU.DXHX202407059
5. [5]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
6. [6]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
7. [7]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
8. [8]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
9. [9]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
10. [10]
  Lilong Gao , Yuhao Zhai , Dongdong Zhang , Linjun Huang , Kunyan Sui . Exploration of Thiol-Ene Click Polymerization in Polymer Chemistry Experiment Teaching. University Chemistry, 2025, 40(4): 87-93. doi: 10.12461/PKU.DXHX202405143
11. [11]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
12. [12]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
13. [13]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
14. [14]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
15. [15]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
16. [16]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
17. [17]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
18. [18]
  Zunxiang Zeng , Yuling Hu , Yufei Hu , Hua Xiao . Analysis of Plant Essential Oils by Supercritical CO₂Extraction with Gas Chromatography-Mass Spectrometry: An Instrumental Analysis Comprehensive Experiment Teaching Reform. University Chemistry, 2024, 39(3): 274-282. doi: 10.3866/PKU.DXHX202309069
19. [19]
  Houjin Li , Lin Wu , Xingwen Sun , Yuan Zheng , Zhanxiang Liu , Shuanglian Cai , Ying Xiong , Guangao Yu , Qingwen Liu , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Specification Suggestions for Organic Chemical Chromatography Experiments. University Chemistry, 2025, 40(5): 93-105. doi: 10.12461/PKU.DXHX202408100
20. [20]
  Yujing Chen , Hongqun Ouyang , Dan Zhao , Yanyan Chu , Zhengping Qiao . Recommendations for the Content and Instruction of the Physical Chemistry Experiment “Construction of Ternary Liquid-Liquid Phase Diagrams”. University Chemistry, 2025, 40(7): 359-366. doi: 10.12461/PKU.DXHX202409120

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(796)
HTML views(53)

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