Enantiomeric resolution of a series of chiral sulfoxides by high-performance liquid chromatography on polysaccharide-based columns with multimodal elution

被引:43
作者
Cass, QB [1 ]
Batigalhia, F [1 ]
机构
[1] Univ Fed Sao Carlos, Dept Quim, BR-13565970 Sao Carlos, SP, Brazil
关键词
enantiomer separation; stationary phases; LC; sulfoxides;
D O I
10.1016/S0021-9673(02)01451-6
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
The enantiomeric resolution of a series of 20 asymmetric sulfoxides was systematically investigated by HPLC using multimodal elution with amylose tris[(S)-1-phenylethylcarbamate], amylose tris(3,5-dimethoxyphenylcarbamate) and amylose and cellulose tris(3,5-dimethylphenylcarbamate) phases. The sulfoxide series was composed of aromatic, olefinic and ketosulfoxides, sulfinyl acids and esters. This work has shown that enantio selectivity and enantioresolution of the poly saccharide-based columns can be achieved by changing the type and composition of the mobile phase, widening the applicability of these chiral phases. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:445 / 452
页数:8
相关论文
共 32 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]  
AboulEnein HY, 1996, CHIRALITY, V8, P153, DOI 10.1002/(SICI)1520-636X(1996)8:1<153::AID-CHIR23>3.0.CO
[3]  
2-L
[4]   Selective and mild oxidation of sulfides to sulfoxides by oxodiperoxo molybdenum complexes adsorbed onto silica gel [J].
Batigalhia, F ;
Zaldini-Hernandes, M ;
Ferreira, AG ;
Malvestiti, I ;
Cass, QB .
TETRAHEDRON, 2001, 57 (48) :9669-9676
[5]   APPLICATIONS OF SULFOXIDES TO ASYMMETRIC-SYNTHESIS OF BIOLOGICALLY-ACTIVE COMPOUNDS [J].
CARRENO, MC .
CHEMICAL REVIEWS, 1995, 95 (06) :1717-1760
[6]  
Cass QB, 1997, CHIRALITY, V9, P109, DOI 10.1002/(SICI)1520-636X(1997)9:2<109::AID-CHIR6>3.0.CO
[7]  
2-C
[8]   The use of a polysaccharide-based column on multimodal elution [J].
Cass, QB ;
Degani, ALG ;
Cassiano, N .
JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES, 2000, 23 (07) :1029-1038
[9]   Enantiomeric determination of pantoprazole in human plasma by multidimensional high-performance liquid chromatography [J].
Cass, QB ;
Degani, ALG ;
Cassiano, NM ;
Pedrazolli, J .
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 2002, 766 (01) :153-160
[10]   An enantioselective assay for (±)-modafinil [J].
Cass, QB ;
Kohn, CK ;
Calafatti, SA ;
Aboul-Enein, HY .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2001, 26 (01) :123-130