Chiral ligand-exchange chromatography for separation of three stereoisomers of octahydroindole-2-carboxylic acid

被引:11
作者
Sun, SY
Jia, YZ
Zeng, N
Li, FM [1 ]
机构
[1] Shenyang Pharmaceut Univ, Shenyang 110016, Peoples R China
[2] Shanghai Inst Pharmaceut Ind, Shanghai 200437, Peoples R China
关键词
column liquid chromatography; diastereo-enantio separation; chiral mobile phase; ligand-exchange; octohydroindole-2-carboxylic acid;
D O I
10.1365/s10337-006-0752-7
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
A novel HPLC method is described for separation of the three stereoisomers of octahydroinclole-2-carboxylic acid (Oic), an intermediate in the synthesis of perindopril. The chiral mobile phase contained the complex of Cu(II) with the optically active selector L-phenylalaninamide (L-PheA), and an ion-pair reagent, sodium 1-octanesulfonate. The effects of the concentrations of the Cu(II)-L-PheA complex and the ion-pair reagent, mobile phase pH, ionic strength, acetonitrile content, and column temperature were studied. Satisfactory resolution was achieved for three stereoisomers, RRR-, SSS-, and SRR-Oic.
引用
收藏
页码:331 / 335
页数:5
相关论文
共 18 条
[1]   COPPER(II) COMPLEXES OF DIAMINO-DIAMIDO-TYPE LIGANDS AS CHIRAL ELUENTS IN THE ENANTIOMERIC SEPARATION OF D,L-DANSYLAMINO ACIDS BY REVERSED-PHASE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].
ARMANI, E ;
DOSSENA, A ;
MARCHELLI, R ;
VIRGILI, R .
JOURNAL OF CHROMATOGRAPHY, 1988, 441 (02) :275-286
[2]   BIS(L-AMINO ACID AMIDATO)COPPER(II) COMPLEXES AS CHIRAL ELUENTS IN THE ENANTIOMERIC SEPARATION OF D,L-DANSYLAMINO ACIDS BY REVERSED-PHASE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].
ARMANI, E ;
BARAZZONI, L ;
DOSSENA, A ;
MARCHELLI, R .
JOURNAL OF CHROMATOGRAPHY, 1988, 441 (02) :287-298
[3]  
Cendrowska Iwona, 2003, Acta Pol Pharm, V60, P141
[4]  
Davankov V.A., 1988, Ligand Exchange Chromatography
[5]   Enantioselective ligand exchange in modern separation techniques [J].
Davankov, VA .
JOURNAL OF CHROMATOGRAPHY A, 2003, 1000 (1-2) :891-915
[6]  
Davankov VA, 2003, METH MOL B, V243, P207
[7]   DETERMINATION OF THE ENANTIOMERS OF ALPHA-AMINO-ACIDS AND ALPHA-AMINO-ACID AMIDES BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY WITH A CHIRAL MOBILE PHASE [J].
DUCHATEAU, A ;
CROMBACH, M ;
AUSSEMS, M ;
BONGERS, J .
JOURNAL OF CHROMATOGRAPHY, 1989, 461 :419-428
[8]   Chiral discrimination of Dns- and unmodified D,L-amino acids by copper(II) complexes of terdentate ligands in high-performance liquid chromatography [J].
Galaverna, G ;
Corradini, R ;
Dossena, A ;
Chiavaro, E ;
Marchelli, R ;
Dallavalle, F ;
Folesani, G .
JOURNAL OF CHROMATOGRAPHY A, 1998, 829 (1-2) :101-113
[9]  
Galaverna G, 1996, CHIRALITY, V8, P189
[10]   Chiral separation of amino acids by copper(II) complexes of tetradentate diaminodiamido-type ligands added to the eluent in reversed-phase high-performance liquid chromatography: a ligand exchange mechanism [J].
Galaverna, G ;
Corradini, R ;
Dallavalle, F ;
Folesani, G ;
Dossena, A ;
Marchelli, R .
JOURNAL OF CHROMATOGRAPHY A, 2001, 922 (1-2) :151-163