Separation and enantioseparation of derivatized amino acids and biogenic amines by high-performance liquid chromatography with reversed and chiral stationary phases

被引:13
作者
Shpigun, OA [1 ]
Shapovalova, EN [1 ]
Ananieva, IA [1 ]
Pirogov, AV [1 ]
机构
[1] Moscow MV Lomonosov State Univ, Dept Chem, Div Analyt Chem, Moscow 119899, Russia
关键词
enantiomer separation; mobile phase composition; octanol-water partition coefficients; amino acids; amines;
D O I
10.1016/S0021-9673(02)01468-1
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
This study demonstrates that an ainino-beta-cyclodextrin-bonded phase column exhibits enantioselectivity for various amino acid derivatives. Mixtures of methanol, acetonitrile, tetrahydrofuran or dioxan and triethylamine buffers (pH 4.0-7.0) were used as mobile phases. The effect of the mobile phase on the resolution process was studied by varying the mobile phase composition (type and percentage of organic modifiers, pH, and ionic strength of the buffer solution). The 1-octanol-water partition coefficients are calculated and tabulated for 16 derivatized amino acids. The chromatographic data for 42 pairs of derivatized amino acids resolved on the amino-beta-cyclodextrin-bonded phase are summarised. The separation of adrenaline, noradrenaline and amphetamine on a novel vancomycin stationary phase is demonstrated. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:191 / 199
页数:9
相关论文
共 18 条
[1]  
*ADV SEP TECHN, 1999, CYCL CHIR SEP
[2]  
ANANEVA IA, 2002, ZH ANAL KHIM, V57, P393
[3]  
[Anonymous], 1999, CHIR HDB
[4]  
ARMSTRONG DW, 1987, CHROMATOGR FORUM, V2, P43
[5]   Facile liquid chromatographic enantioresolution of native amino acids and peptides using a teicoplanin chiral stationary phase [J].
Berthod, A ;
Liu, YB ;
Bagwill, C ;
Armstrong, DW .
JOURNAL OF CHROMATOGRAPHY A, 1996, 731 (1-2) :123-137
[6]   FACILE RESOLUTION OF N-TERT-BUTOXY-CARBONYL AMINO-ACIDS - THE IMPORTANCE OF ENANTIOMERIC PURITY IN PEPTIDE-SYNTHESIS [J].
CHANG, SC ;
WANG, LR ;
ARMSTRONG, DW .
JOURNAL OF LIQUID CHROMATOGRAPHY, 1992, 15 (09) :1411-1429
[7]   SYNTHESIS OF OPTICALLY-ACTIVE COMPOUNDS - A LARGE-SCALE PERSPECTIVE [J].
CROSBY, J .
TETRAHEDRON, 1991, 47 (27) :4789-4846
[8]   A STUDY OF THE SEPARATION OF ENANTIOMERS OF SOME AROMATIC CARBOXYLIC-ACIDS BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY ON A BETA-CYCLODEXTRIN-BONDED STATIONARY PHASE [J].
FEITSMA, KG ;
BOSMAN, J ;
DRENTH, BFH ;
DEZEEUW, RA .
JOURNAL OF CHROMATOGRAPHY, 1985, 333 (01) :59-68
[9]   Relative hydrophobicity of organic compounds measured by partitioning in aqueous two-phase systems [J].
Gulyaeva, N ;
Zaslavsky, A ;
Lechner, P ;
Chait, A ;
Zaslavsky, B .
JOURNAL OF CHROMATOGRAPHY B, 2000, 743 (1-2) :187-194
[10]   STRUCTURAL FACTORS AFFECTING CHIRAL RECOGNITION AND SEPARATION ON BETA-CYCLODEXTRIN BONDED PHASES [J].
HAN, SM ;
HAN, YI ;
ARMSTRONG, DW .
JOURNAL OF CHROMATOGRAPHY, 1988, 441 (02) :376-381