Functionalities tuned enantioselectivity of phenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC

被引：10

作者：

Tang, Jian ^{[1
]}

Lin, Yuzhou ^{[1
]}

Yang, Bo ^{[1
]}

Zhou, Jie ^{[1
]}

Tang, Weihua ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Sch Chem Engn, 200 Xiaolingwei St, Nanjing 210094, Jiangsu, Peoples R China

来源：

CHIRALITY | 2017年 / 29卷 / 09期

基金：

国家教育部博士点专项基金资助; 中国国家自然科学基金;

关键词：

chiral separation; enantioselectivity; high-performance liquid chromatography; phenylcarbamate cyclodextrin; PERFORMANCE LIQUID-CHROMATOGRAPHY; ACID-DERIVATIVES; AMINO-ACIDS; ENANTIOSEPARATION; SEPARATION; ENANTIOMERS; CHEMISTRY;

D O I：

10.1002/chir.22732

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The mixed chloro-and methyl-functionalities can greatly modulate the enantioselectivities of phenylcarbamate cyclodextrin (CD) clicked chiral stationary phases (CSPs). A comparison study is herein reported for per(4-chloro-3-methyl) phenylcarbamate and per(2-chloro-5-methyl) phenylcarbamate beta-CD clicked CSPs (i. e., CCC4M3-CSP and CCC2M5-CSP). The enantioselectivity dependence on column temperature was studied in both normal-phase and reversed-phase mode high performance liquid chromatography (HPLC). The thermodynamic study revealed that the stronger intermolecular interactions can be formed between CCC4M3-CSP and chiral solutes to drive the chiral separation. The higher enantioselectivities of CCC4M3-CSP were further demonstrated with the enantioseparation of 17 model racemates in HPLC.

引用

页码：566 / 573

页数：8

共 30 条

[1] Enantioselective separation of dansyl-DL-amino acids and some racemates on "click" functionalized native α-cyclodextrin based sub-2 μm columns [J].

Ai, Feng ;

Wang, Yong ;

Chen, Hui ;

Yang, Yanhui ;

Tan, Timothy Thatt Yang ;

Ng, Siu-Choon .

ANALYST, 2013, 138 (08) :2289-2294

[2] CHLOROMETHYLPHENYLCARBAMATE DERIVATIVES OF CELLULOSE AS CHIRAL STATIONARY PHASES FOR HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].

CHANKVETADZE, B ;

YASHIMA, E ;

OKAMOTO, Y .

JOURNAL OF CHROMATOGRAPHY A, 1994, 670 (1-2) :39-49

[3] Synthesis and chromatographic properties of a novel chiral stationary phase derived from heptakis(6-azido-6-deoxy-2,3-di-O-phenylcarbamoylated)-β-cyclodextrin immobilized onto amino-functionalized silica gel via multiple urea linkages [J].

Chen, L ;

Zhang, LF ;

Ching, CB ;

Ng, SC .

JOURNAL OF CHROMATOGRAPHY A, 2002, 950 (1-2) :65-74

[4] Effect of phase ratio on van't Hoff analysis in reversed-phase liquid chromatography, and phase-ratio-independent estimation of transfer enthalpy [J].

Chester, TL ;

Coym, JW .

JOURNAL OF CHROMATOGRAPHY A, 2003, 1003 (1-2) :101-111

[5] Application of click chemistry on preparation of separation materials for liquid chromatography [J].

Chu, Changhu ;

Liu, Renhua .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) :2177-2188

[6] Study of the mechanism of enantioseparation -: Part VI:: Thermodynamic study of HPLC separation of some enantiomers of phenylcarbamic acid derivatives on a (SS) Whelk-O 1 column [J].

Dungelová, J ;

Lehotay, J ;

Krupcík, J ;

Cizmárik, J ;

Armstrong, DW .

JOURNAL OF SEPARATION SCIENCE, 2004, 27 (12) :983-990

[7] Development of HPLC Chiral Stationary Phases Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid and Their Applications [J].

Hyun, Myung Ho .

CHIRALITY, 2015, 27 (09) :576-588

[8] Polymethacrylate monoliths with immobilized poly-3-mercaptopropyl methylsiloxane film for high-coverage surface functionalization by thiol-ene click reaction [J].

Javier Carrasco-Correa, Enrique ;

Ramis-Ramos, Guillermo ;

Manuel Herrero-Martinez, Jose ;

Laemmerhofer, Michael .

JOURNAL OF CHROMATOGRAPHY A, 2014, 1367 :123-130

[9]

Kolb HC, 2001, ANGEW CHEM INT EDIT, V40, P2004, DOI 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO

[10]

2-5

← 1 2 3 →