Urea bonded cyclodextrin derivatives onto silica for chiral HPLC

被引:64
作者
Muderawan, I. Wayan
Ong, Teng-Teng
Ng, Siu-Choon [1 ]
机构
[1] Nanyang Technol Univ, Div Chem & Biomol Engn, Singapore 637722, Singapore
[2] Chiral Sci & Technol Pte Ltd, Singapore, Singapore
关键词
chiral stationary phases; enantioseparation; high performance liquid chromatography; perfunctionalised cyclodextrin; urea linkage;
D O I
10.1002/jssc.200500491
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Several structurally well-defined perfunctionalised cyclodextrin chiral stationary phases (CD CSPs) for high performance liquid chromatography have been successfully prepared by immobilisation of perfunctionalised cyclodextrins on silica through urea linkage(s) using the Staudinger reaction. These CSPs show high chiral recognition efficiency and are utilised in the resolution of various types of racemic compounds. This paper reviews the development of sixteen perfunctionalised cyclodextrin-based CSPs, their preparation, and their application to enantioseparation of seventy-seven racemic compounds under a range of separation conditions.
引用
收藏
页码:1849 / 1871
页数:23
相关论文
共 63 条
[1]   CHIRALITY IN BIOACTIVE AGENTS AND ITS PITFALLS [J].
ARIENS, EJ .
TRENDS IN PHARMACOLOGICAL SCIENCES, 1986, 7 (05) :200-205
[2]   CYCLODEXTRIN BONDED PHASES FOR THE LIQUID-CHROMATOGRAPHIC SEPARATION OF OPTICAL, GEOMETRICAL, AND STRUCTURAL ISOMERS [J].
ARMSTRONG, DW ;
DEMOND, W .
JOURNAL OF CHROMATOGRAPHIC SCIENCE, 1984, 22 (09) :411-415
[3]   DERIVATIZED CYCLODEXTRINS FOR NORMAL-PHASE LIQUID-CHROMATOGRAPHIC SEPARATION OF ENANTIOMERS [J].
ARMSTRONG, DW ;
STALCUP, AM ;
HILTON, ML ;
DUNCAN, JD ;
FAULKNER, JR ;
CHANG, SC .
ANALYTICAL CHEMISTRY, 1990, 62 (15) :1610-1615
[4]  
ARMSTRONG DW, Patent No. 4539399
[5]   BETA-CYCLODEXTRIN CHIRAL STATIONARY PHASES FOR LIQUID-CHROMATOGRAPHY - EFFECT OF THE SPACER ARM ON CHIRAL RECOGNITION [J].
BERTHOD, A ;
CHANG, CD ;
ARMSTRONG, DW .
TALANTA, 1993, 40 (09) :1367-1373
[6]   SPECTROPHOTOMETRIC AND POLARIMETRIC DETECTORS IN LIQUID-CHROMATOGRAPHY FOR THE DETERMINATION OF ENANTIOMER RATIOS IN COMPLEX-MIXTURES [J].
BOEHME, W ;
WAGNER, G ;
OEHME, U ;
PRIESNITZ, U .
ANALYTICAL CHEMISTRY, 1982, 54 (04) :709-711
[7]   Cyclodextrins and enantiomeric separations of drugs by liquid chromatography and capillary electrophoresis: Basic principles and new developments [J].
Bressolle, F ;
Audran, M ;
Pham, TN ;
Vallon, JJ .
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 1996, 687 (02) :303-336
[8]   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
[9]  
CHEN L, 2002, THESIS NATL U SINGAP
[10]   Effect of mobile phase composition on the separation of propranolol enantiomers using a perphenylcarbamate β-cyclodextrin bonded chiral stationary phase [J].
Ching, CB ;
Fu, P ;
Ng, SC ;
Xu, YK .
JOURNAL OF CHROMATOGRAPHY A, 2000, 898 (01) :53-61