Organic-inorganic hybrid materials for efficient enantioseparation using cellulose 3,5-dimethylphenylcarbamate and tetraethyl orthosilicate

被引:34
作者
Ikai, Tomoyuki [2 ]
Yamamoto, Chiyo [3 ]
Kamigaito, Masami [2 ]
Okamoto, Yoshio [1 ]
机构
[1] Nagoya Univ, EcoTopia Sci Inst, Chikusa Ku, Nagoya, Aichi 4648603, Japan
[2] Nagoya Univ, Grad Sch Engn, Dept Appl Chem, Chikusa Ku, Nagoya, Aichi 4648603, Japan
[3] Suzuka Natl Coll Technol, Shiroko, Suzuka 5100294, Japan
关键词
chiral packing material; chiral resolution; organic-inorganic hybrid composites; silicon; sol-gel processes;
D O I
10.1002/asia.200800022
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The hybrid bead-type chiral packing material (CPM) for preparative enantioseparation has been prepared from the cellulose 3,5-dimethylphenylcarbamate containing a small number of 3-(triethoxysily)propyl groups in the presence of tetraethyl orthosilicate, by a sol-gel reaction in an aqueous surfactant solution. The obtained hybrid bead-type CPM was packed into a column and evaluated by high-performance liquid chromatography. When compared with the commercially available Chiralpak IB, which is prepared by the immobilization of cellulose 3,5-dimethylphenylcarbamate on silica gel, the hybrid bead-type CPM was shown to exhibit a similar chiral recognition and possess a higher loading capacity.
引用
收藏
页码:1494 / 1499
页数:6
相关论文
共 49 条
[1]   High-performance liquid chromatographic enantioseparation of drags containing multiple chiral centers on polysaccharide-type chiral stationary phases [J].
Aboul-Enein, HY .
JOURNAL OF CHROMATOGRAPHY A, 2001, 906 (1-2) :185-193
[2]   Putting chirality to work: The strategy of chiral switches [J].
Agranat, I ;
Caner, H ;
Caldwell, A .
NATURE REVIEWS DRUG DISCOVERY, 2002, 1 (10) :753-768
[3]   Mechanistic principles in chiral separations using liquid chromatography and capillary electrophoresis [J].
Ali, I ;
Kumerer, K ;
Aboul-Enein, HY .
CHROMATOGRAPHIA, 2006, 63 (7-8) :295-307
[4]   Impact of immobilized polysaccharide chiral stationary phases on enantiomeric separations [J].
Ali, I ;
Aboul-Enein, HY .
JOURNAL OF SEPARATION SCIENCE, 2006, 29 (06) :762-769
[5]   Preparative chiral chromatographic resolution of enantiomers in drug discovery [J].
Andersson, S ;
Allenmark, SG .
JOURNAL OF BIOCHEMICAL AND BIOPHYSICAL METHODS, 2002, 54 (1-3) :11-23
[6]  
ARMSTRONG DW, 1987, ANAL CHEM, V59, P84
[7]  
Bojarski J, 1996, BIOMED CHROMATOGR, V10, P297, DOI 10.1002/(SICI)1099-0801(199611)10:6<297::AID-BMC617>3.0.CO
[8]  
2-M
[9]   Trends in the development of chiral drugs [J].
Caner, H ;
Groner, E ;
Levy, L ;
Agranat, I .
DRUG DISCOVERY TODAY, 2004, 9 (03) :105-110
[10]   Influence of vinyl monomers and temperature on immobilization of cellulose 3,5-dimethylphenylcarbamate onto silica gel as chiral stationary phases for high-performance liquid chromatography [J].
Chen, XM ;
Yamamoto, C ;
Okamoto, Y .
JOURNAL OF CHROMATOGRAPHY A, 2006, 1104 (1-2) :62-68