Enantiomer separation of amino compounds by a novel chiral stationary phase derived from crown ether

被引:128
作者
Machida, Y [1 ]
Nishi, H [1 ]
Nakamura, K [1 ]
Nakai, H [1 ]
Sato, T [1 ]
机构
[1] Tanabe Seiyaku Co Ltd, Analyt Res Lab, Yodogawa Ku, Osaka 532, Japan
关键词
enantiomer separation; stationary phases; LC; crown ethers; amino acids; amino alcohols; primary amines;
D O I
10.1016/S0021-9673(98)00013-2
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
A novel chiral stationary phase (CSP-18C6I) was prepared by immobilizing (+)-18-crown-6 tetracarboxylic acid on 3-aminopropylsilanized silica-gel to separate enantiomers of drugs having a primary amino group. The chiral crown ether was combined with 5-aminopropyl silica gel (0.85 mmol of amine per gram of gel) to provide CSP-18C61 having a chiral selector loading of 0.26 mmol per gram of gel. This CSP-18C6I showed good chiral recognition for thirteen out of eighteen or-amino acids and seven racemic aminoalcohols using a dilute aqueous solution of perchloric acid as the eluent. Afloqualone (a muscle relaxant), primaquine (an antimalarial), and 1-(1-naphthyl)ethylamine (1-NEA) were resolved on the CSP-18C61. Furthermore, alanine-beta-naphthylamide (Ala-beta-NA), which is hydrophobic and did not elute within 60 min by the commercially available CROWNPAK CR(+) with 15% methanol and a column temperature of 40 degrees C, was successfully enantioseparated by the novel CSP-18C6I. (C) 1998 Elsevier Science B.V.
引用
收藏
页码:85 / 92
页数:8
相关论文
共 23 条
[1]  
[Anonymous], 1992, Chirality, V4, P338
[2]   MACROCYCLIC ANTIBIOTICS AS A NEW CLASS OF CHIRAL SELECTORS FOR LIQUID-CHROMATOGRAPHY [J].
ARMSTRONG, DW ;
TANG, YB ;
CHEN, SS ;
ZHOU, YW ;
BAGWILL, C ;
CHEN, JR .
ANALYTICAL CHEMISTRY, 1994, 66 (09) :1473-1484
[3]   USE OF A MACROCYCLIC ANTIBIOTIC, RIFAMYCIN-B, AND INDIRECT DETECTION FOR THE RESOLUTION OF RACEMIC AMINO-ALCOHOLS BY CE [J].
ARMSTRONG, DW ;
RUNDLETT, K ;
REID, GL .
ANALYTICAL CHEMISTRY, 1994, 66 (10) :1690-1695
[4]  
ARMSTRONG DW, 1995, CHIRALITY, V7, P145
[5]   EVALUATION OF A NEW POLAR ORGANIC HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC MOBILE PHASE FOR CYCLODEXTRIN-BONDED CHIRAL STATIONARY PHASES [J].
CHANG, SC ;
REID, GL ;
CHEN, S ;
CHANG, CD ;
ARMSTRONG, DW .
TRAC-TRENDS IN ANALYTICAL CHEMISTRY, 1993, 12 (04) :144-153
[6]   SYNTHESIS AND METAL-ION COMPLEXATION BEHAVIOR OF POLYCARBOXYLATE 18-CROWN-6 ETHERS DERIVED FROM TARTARIC ACID [J].
DUTTON, PJ ;
FYLES, TM ;
MCDERMID, SJ .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (05) :1097-1108
[7]   ENANTIOMERIC SEPARATIONS IN CAPILLARY ZONE ELECTROPHORESIS USING A CHIRAL CROWN-ETHER [J].
KUHN, R ;
STEINMETZ, C ;
BEREUTER, T ;
HAAS, P ;
ERNI, F .
JOURNAL OF CHROMATOGRAPHY A, 1994, 666 (1-2) :367-373
[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 SEPARATIONS BY HOST-GUEST COMPLEXATION WITH CYCLODEXTRIN AND CROWN-ETHER IN CAPILLARY ZONE ELECTROPHORESIS [J].
KUHN, R ;
STOECKLIN, F ;
ERNI, F .
CHROMATOGRAPHIA, 1992, 33 (1-2) :32-36
[10]   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