Chiral separations in polar organic solvent chromatography: Updating a screening strategy with new chlorine-containing 14 polysaccharide-based selectors

被引:59
作者
Ates, Hasret [1 ]
Mangelings, Debby [1 ]
Heyden, Yvan Vander [1 ]
机构
[1] Vrije Univ Brussels, Dept Analyt Chem & Pharmaceut Technol, B-1090 Brussels, Belgium
来源
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES | 2008年 / 875卷 / 01期
关键词
Chlorine-containing polysaccharide; stationary phases; Sepapak (R)-2; Sepapak (R)-3; Enantioselectivity; Chiral analyses; Polar organic solvent chromatography;
D O I
10.1016/j.jchromb.2008.07.038
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
The screening conditions of an existing column and mobile phase selection strategy for chiral drug substances in polar organic solvent liquid chromatography (POSC) were tested for their applicability on two new chlorine-containing polysaccharide-based stationary phases. The selectors of these phases are cellulose tris(3-chloro-4-methylphenylcarbamate) and amylose tris(5-chloro-2-methylphenylcarbamate). The enantioselectivity of these phases is compared to that of the four phases (Chiralpak (R) AD-RH, Chiralcel (R) OD-RH, Chiralpak (R) AS-RH and Chiralcel (R) OJ-RH) used in the earlier defined strategy. A test set of 62 structurally diverse chiral drug substances is anal zed using the screening conditions of the strategy on the six phases. The results confirm that the acetonitrile-based mobile phase provides a higher success rate and better resolutions than the methanol-based also on the new phases. However, the importance of the methanol-based mobile phase cannot be neglected for complementarity, reasons: the two mobile phases insure enantioselectivity for different compounds. A third (ethanol-based) mobile phase, not part of the strategy, was also used to screen the two new phases. The joint results led to different possibilities to upgrade the current screening strategy so that improved success rates are obtained. The chlorine-containing chiral stationary phases demonstrated to have an added value to the screening process since they provided enantioresolution for compounds not resolved by non-chlorine-containing ones. (c) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:57 / 64
页数:8
相关论文
共 33 条
[1]   Chiral separations of piperidine-2,6-dione analogues on Chiralpak IA and Chiralpak IB columns by using HPLC [J].
Ali, Imran ;
Naim, Lahoucine ;
Ghanem, Ashraf ;
Aboul-Enein, Hassan Y. .
TALANTA, 2006, 69 (04) :1013-1017
[2]   Fast generic chiral separation strategies using electrophoretic and liquid chromatographic techniques [J].
Ates, Hasret ;
Mangelings, Debby ;
Heyden, Yvan Vander .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2008, 48 (02) :288-294
[3]   Enantiomer separation of drugs by capillary electromigration techniques [J].
Blaschke, G ;
Chankvetadze, B .
JOURNAL OF CHROMATOGRAPHY A, 2000, 875 (1-2) :3-25
[4]   Comparative performances of selected chiral HPLC, SFC, and CE systems with a chemically diverse sample set [J].
Borman, P ;
Boughtflower, B ;
Cattanach, K ;
Crane, K ;
Freebairn, K ;
Jonas, G ;
Mutton, I ;
Patel, A ;
Sanders, M ;
Thompson, D .
CHIRALITY, 2003, 15 :S1-S12
[5]   3-fluoro-, 3-chloro- and 3-bromo-5-methylphenylcarbamates of cellulose and amylose as chiral stationary phases for high-performance liquid chromatographic enantioseparation [J].
Chankvetadze, B ;
Chankvetadze, L ;
Sidamonidze, S ;
Kasashima, E ;
Yashima, E ;
Okamoto, Y .
JOURNAL OF CHROMATOGRAPHY A, 1997, 787 (1-2) :67-77
[6]   DIMETHYLPHENYLCARBAMATES, DICHLOROPHENYLCARBAMATES AND CHLOROMETHYLPHENYLCARBAMATES OF AMYLOSE AS CHIRAL STATIONARY PHASES FOR HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].
CHANKVETADZE, B ;
YASHIMA, E ;
OKAMOTO, Y .
JOURNAL OF CHROMATOGRAPHY A, 1995, 694 (01) :101-109
[7]   Comparative enantioseparation of selected chiral drugs on four different polysaccharide-type chiral stationary phases using polar organic mobile phases [J].
Chankvetadze, B ;
Kartozia, I ;
Yamamoto, C ;
Okamoto, Y .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2002, 27 (3-4) :467-478
[8]   High performance liquid chromatography enantioseparation of chiral pharmaceuticals using tris(chloro-methylphenylcarbamate)s of cellulose [J].
Chankvetadze, B ;
Chankvetadze, L ;
Sidamonidze, S ;
Yashima, E ;
Okamoto, Y .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 1996, 14 (8-10) :1295-1303
[9]   Immobilized halogenophenylcarbamate derivatives of cellulose as novel stationary phases for enantioselective drug analysis [J].
Francotte, E ;
Huynh, D .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2002, 27 (3-4) :421-429
[10]  
Francotte E., 2006, CHIRALITY DRUG RES, P155