Enantiomeric separations of primary amino compounds by non-aqueous capillary zone electrophoresis with a chiral crown ether

被引:66
作者
Mori, Y [1 ]
Ueno, K [1 ]
Umeda, T [1 ]
机构
[1] SHIONOGI & CO LTD,SHIONOGI RES LABS,FUKUSHIMA KU,OSAKA 553,JAPAN
关键词
enantiomer separation; chiral crown ethers; host-guest complexation; 1-naphthylethylamine; 1-phenylethylamine; phenylalanine; DOPA; tryptophan; norephedrine; noradrenaline; 2-amino-1,2-diphenylethanol;
D O I
10.1016/S0021-9673(96)00674-7
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
The enantiomeric separation by capillary electrophoresis (CE) in non-aqueous media was examined. The enantiomeric separations of eight primary amino compounds including aromatic amines, amino acids and amino alcohols were achieved by CE in formamide containing a chiral crown ether, (+)-18-crown-6 tetracarboxylic acid. The addition of tetra-n-butylammonium perchlorate as a supporting electrolyte to the electrophoretic solution improved the separation efficiency and gave the baseline enantiomeric separation of DL-1-phenylethylamine which has not been separated by any other separation mode of CE yet.
引用
收藏
页码:328 / 332
页数:5
相关论文
共 16 条
[1]   MOLECULAR RECEPTORS - STRUCTURAL EFFECTS AND SUBSTRATE RECOGNITION IN BINDING OF ORGANIC AND BIOGENIC AMMONIUM-IONS BY CHIRAL POLYFUNCTIONAL MACROCYCLIC POLYETHERS BEARING AMINO-ACID AND OTHER SIDE-CHAINS .1. [J].
BEHR, JP ;
LEHN, JM ;
VIERLING, P .
HELVETICA CHIMICA ACTA, 1982, 65 (06) :1853-1867
[2]   COMPARISON OF SEPARATION SELECTIVITY IN AQUEOUS AND NONAQUEOUS CAPILLARY ELECTROPHORESIS [J].
BJORNSDOTTIR, I ;
HANSEN, SH .
JOURNAL OF CHROMATOGRAPHY A, 1995, 711 (02) :313-322
[3]   DETERMINATION OF THE ENANTIOMERIC PURITY OF 5,6-DIHYDROXY-2-AMINOTETRALIN BY HIGH-PERFORMANCE CAPILLARY ELECTROPHORESIS WITH CROWN-ETHER AS CHIRAL SELECTOR [J].
CASTELNOVO, P ;
ALBANESI, C .
JOURNAL OF CHROMATOGRAPHY A, 1995, 715 (01) :143-149
[4]   USE OF NEGATIVELY CHARGED SULFOBUTYL ETHER-BETA-CYCLODEXTRIN FOR ENANTIOMERIC SEPARATION BY CAPILLARY ELECTROPHORESIS [J].
DESIDERIO, C ;
FANALI, S .
JOURNAL OF CHROMATOGRAPHY A, 1995, 716 (1-2) :183-196
[5]   SEPARATION OF OPTICAL ISOMERS BY CAPILLARY ZONE ELECTROPHORESIS BASED ON HOST GUEST COMPLEXATION WITH CYCLODEXTRINS [J].
FANALI, S .
JOURNAL OF CHROMATOGRAPHY, 1989, 474 (02) :441-446
[6]   THERMODYNAMIC AND KINETIC DATA FOR CATION MACROCYCLE INTERACTION [J].
IZATT, RM ;
BRADSHAW, JS ;
NIELSEN, SA ;
LAMB, JD ;
CHRISTENSEN, JJ .
CHEMICAL REVIEWS, 1985, 85 (04) :271-339
[7]   N-METHYLFORMAMIDE AS A SEPARATION MEDIUM IN CAPILLARY ELECTROPHORESIS [J].
JANSSON, M ;
ROERAADE, J .
CHROMATOGRAPHIA, 1995, 40 (3-4) :163-169
[8]   POTENTIAL AND LIMITATIONS OF AN OPTICALLY-ACTIVE CROWN-ETHER FOR CHIRAL SEPARATION IN CAPILLARY ZONE ELECTROPHORESIS [J].
KUHN, R ;
WAGNER, J ;
WALBROEHL, Y ;
BEREUTER, T .
ELECTROPHORESIS, 1994, 15 (06) :828-834
[9]   CHIRAL RECOGNITION AND ENANTIOMERIC RESOLUTION BASED ON HOST GUEST COMPLEXATION WITH CROWN ETHERS IN CAPILLARY ZONE ELECTROPHORESIS [J].
KUHN, R ;
ERNI, F ;
BEREUTER, T ;
HAUSLER, J .
ANALYTICAL CHEMISTRY, 1992, 64 (22) :2815-2820
[10]   EVALUATION OF AN OPTICALLY-ACTIVE CROWN-ETHER FOR THE CHIRAL SEPARATION OF DIPEPTIDES AND TRIPEPTIDES [J].
KUHN, R ;
RIESTER, D ;
FLECKENSTEIN, B ;
WIESMULLER, KH .
JOURNAL OF CHROMATOGRAPHY A, 1995, 716 (1-2) :371-379