Liquid chromatographic resolution of racemic amines, amino alcohols and related compounds on a chiral crown ether stationary phase

被引:70
作者
Hyun, MH [1 ]
Han, SC
Lipshutz, BH
Shin, YJ
Welch, CJ
机构
[1] Pusan Natl Univ, Dept Chem, Pusan 609735, South Korea
[2] Pusan Natl Univ, Chem Inst Funct Mat, Pusan 609735, South Korea
[3] Univ Calif Santa Barbara, Dept Chem, Santa Barbara, CA 93106 USA
[4] Merck & Co Inc, Rahway, NJ 07065 USA
关键词
chiral stationary phases; LC; enantiomer separation; amines; amino alcohols; crown ethers;
D O I
10.1016/S0021-9673(02)00431-4
中图分类号
Q5 [生物化学];
学科分类号
071010 [生物化学与分子生物学]; 081704 [应用化学];
摘要
A chiral stationary phase (CSP) based on diphenyl-substituted 1,1'-binaphthyl crown ether was applied in resolving various racemic amines, amino alcohols and alpha-aminocarbonyl compounds including pharmaceutically important compounds such as amphetamine analogues, mexiletine, norepinephrine and norephedrine. The resolution was quite successful. In order to find out the effects of mobile phase additives on the chromatographic resolution behaviors, four selected racemic compounds were resolved on the CSP with the variation of the type and content of organic, acidic and cationic modifiers in aqueous mobile phase and with the variation of column temperature. The resolution behaviors were quite dependent on the type and the content of organic, acidic and cationic modifiers in aqueous mobile phase and on column temperature. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:75 / 83
页数:9
相关论文
共 16 条
[1]
EVALUATION OF A CHIRAL CROWN-ETHER LC COLUMN FOR THE SEPARATION OF RACEMIC AMINES [J].
HILTON, M ;
ARMSTRONG, DW .
JOURNAL OF LIQUID CHROMATOGRAPHY, 1991, 14 (01) :9-28
[2]
Liquid chromatographic resolution of racemic amino acids and their derivatives on a new chiral stationary phase based on crown ether [J].
Hyun, MH ;
Jin, JS ;
Lee, WJ .
JOURNAL OF CHROMATOGRAPHY A, 1998, 822 (01) :155-161
[3]
New chiral crown ether stationary phase for the liquid chromatographic resolution of α-amino acid enantiomers [J].
Hyun, MH ;
Han, SC ;
Lipshutz, BH ;
Shin, YJ ;
Welch, CJ .
JOURNAL OF CHROMATOGRAPHY A, 2001, 910 (02) :359-365
[4]
Hyun MH, 1998, B KOREAN CHEM SOC, V19, P819
[5]
Liquid chromatographic resolution of racemic amines and amino alcohols on a chiral stationary phase derived from crown ether [J].
Hyun, MH ;
Jin, JS ;
Koo, HJ ;
Lee, WJ .
JOURNAL OF CHROMATOGRAPHY A, 1999, 837 (1-2) :75-82
[6]
Separation of the stereoisomers of racemic fluoroquinolone antibacterial agents on a crown-ether-based chiral HPLC stationary phase [J].
Hyun, MH ;
Han, SC ;
Jin, JS ;
Lee, W .
CHROMATOGRAPHIA, 2000, 52 (7-8) :473-476
[7]
The effect of analyte lipophilicity on the resolution of α-amino acids on a HPLC chiral stationary phase based on crown ether [J].
Hyun, MH ;
Jin, JS ;
Han, SC ;
Cho, YJ .
MICROCHEMICAL JOURNAL, 2001, 70 (03) :205-209
[8]
Impact of triethylamine as a mobile phase additive on the resolution of racemic amino acids on an (+)-18-crown-6-tetracarboxylic acid-derived chiral stationary phase [J].
Jin, JS ;
Stalcup, AM ;
Hyun, MH .
JOURNAL OF CHROMATOGRAPHY A, 2001, 933 (1-2) :83-90
[9]
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
[10]
Enantiomer separation of amino compounds by a novel chiral stationary phase derived from crown ether [J].
Machida, Y ;
Nishi, H ;
Nakamura, K ;
Nakai, H ;
Sato, T .
JOURNAL OF CHROMATOGRAPHY A, 1998, 805 (1-2) :85-92