Enantio- and chemo-selective HPLC separations by chiral-achiral tandem-columns approach:: the combination of CHIROBIOTIC TAG™ and SCX columns for the analysis of propionyl camitine and related impurities

被引:22
作者
D'Acquarica, I
Gasparrini, F
Giannoli, B
Badaloni, E
Galletti, B
Giorgi, F
Tinti, MO
Vigevani, A
机构
[1] Univ Roma La Sapienza, Dipartimento Studi Chim & Yecnol Sostanze Biologi, I-00185 Rome, Italy
[2] R&S Sigma Tau SpA, Dipartimento Chim Analit, I-00040 Pomezia, Italy
关键词
tandem-columns chiral-achiral HPLC; CHIROBIOTIC TAG (TM) column; propionyl carnitine; mixed-bed column;
D O I
10.1016/j.chroma.2004.11.004
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
We describe a new tandem-columns chiral-achiral HPLC arrangement by using a chiral column (CHIROBIOTIC TAG(TM)) connected in series with an achiral column (Spherisorb S5 SCX), based on a strong cationic exchange mechanism; this approach is very useful for the analysis of chiral molecules, containing cationic groups in their structures. We used this special combination to develop an easy and convenient procedure for the enantio- and chemo-selective dosage of propionyl L-carnitine (1) and relative impurities (2-6). which allowed for the simultaneous separation and quantitation within 30 min. Under the best chromatographic conditions (acetonitrile-10 mM sodium dihydrogen phosphate 65:35, v/v (pH(a) 6.80) as the mobile phase and UV detection at 205 nm], all the individual peaks were well separated. The applicability of the method, fully validated, was demonstrated by the analysis of a pharmaceutical batch of propionyl L-carnitine, where we found the following contents: 98.5% for 1 (drug substance); 0.1(5)% for 3: 0.1% for 5 and 0.2% for 6. The enantiomeric excess (e.e.%) measured for the drug substance was 98.9%. Finally, a single mixed-bed column, packed with a binary mixture of the chiral and achiral phases, in a 1: 1 ratio, gave similar chromatographic results as the tandem-columns approach, and thus, offered an easy alternative solution to the separation of the considered mixture. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:167 / 173
页数:7
相关论文
共 24 条
[1]   Acute and chronic effects of propinoyl-L-carnitine on the hemodynamics, exercise capacity, and hormones in patients with congestive heart failure [J].
Anand, I ;
Chandrashekhan, Y ;
De Giuli, F ;
Pasini, E ;
Mazzoletti, A ;
Confortini, R ;
Ferrari, R .
CARDIOVASCULAR DRUGS AND THERAPY, 1998, 12 (03) :291-299
[2]   Role of the carbohydrate moieties in chiral recognition on teicoplanin-based LC stationary phases [J].
Berthod, A ;
Chen, XH ;
Kullman, JP ;
Armstrong, DW ;
Gasparrini, F ;
D'Acquarica, I ;
Villani, C ;
Carotti, A .
ANALYTICAL CHEMISTRY, 2000, 72 (08) :1767-1780
[3]   SUPERIORITY OF L-PROPIONYLCARNITINE VS L-CARNITINE IN IMPROVING WALKING CAPACITY IN PATIENTS WITH PERIPHERAL VASCULAR-DISEASE - AN ACUTE, INTRAVENOUS, DOUBLE-BLIND, CROSS-OVER STUDY [J].
BREVETTI, G ;
PERNA, S ;
SABBA, C ;
ROSSINI, A ;
DIUCCIO, VS ;
BERARDI, E ;
GODI, L .
EUROPEAN HEART JOURNAL, 1992, 13 (02) :251-255
[4]  
Cancelliere, 1999, Pharm Sci Technol Today, V2, P484, DOI 10.1016/S1461-5347(99)00218-7
[5]   DETERMINATION OF THE ENANTIOMERS OF VERAPAMIL AND NORVERAPAMIL IN SERUM USING COUPLED ACHIRAL CHIRAL HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].
CHU, YQ ;
WAINER, IW .
JOURNAL OF CHROMATOGRAPHY-BIOMEDICAL APPLICATIONS, 1989, 497 :191-200
[6]   Direct chromatographic resolution of carnitine and O-acylcarnitine enantiomers on a teicoplanin-bonded chiral stationary phase [J].
D'Acquarica, I ;
Gasparrini, F ;
Misiti, D ;
Villani, C ;
Carotti, A ;
Cellamare, S ;
Muck, S .
JOURNAL OF CHROMATOGRAPHY A, 1999, 857 (1-2) :145-155
[7]  
D'Acquarica I., 1997, J HIGH RES CHROMATOG, V20, P261
[8]   HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY AND CAPILLARY ELECTROPHORESIS OF L-CARNITINE AND D-CARNITINE BY PRECOLUMN DIASTEREOMERIC DERIVATIZATION [J].
DEWITT, P ;
DEIAS, R ;
MUCK, S ;
GALLETTI, B ;
MELONI, D ;
CELLETTI, P ;
MARZO, A .
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 1994, 657 (01) :67-73
[9]  
DILISA F, 1992, CURRENT CONCEPTS IN CARNITINE RESEARCH, P27
[10]   TANDEM COLUMNS AND MIXED-BED COLUMNS IN HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY OF PROTEINS [J].
ELRASSI, Z ;
HORVATH, C .
JOURNAL OF CHROMATOGRAPHY, 1986, 359 :255-264