High-performance liquid chromatographic separation of the enantiomers of unusual α-amino acid analogues

被引:44
作者
Péter, A
Olajos, E
Casimir, R
Tourwé, D
Broxterman, QB
Kaptein, B
Armstrong, DW
机构
[1] Attila Jozsef Univ, Dept Inorgan & Analyt Chem, H-6701 Szeged, Hungary
[2] Free Univ Brussels, Eenheid Organ Chem, B-1050 Brussels, Belgium
[3] DSM Res, Organ Chem & Biotechnol Sect, NL-6160 MD Geleen, Netherlands
[4] Univ Missouri, Dept Chem, Rolla, MO 65401 USA
基金
匈牙利科学研究基金会;
关键词
enantiomer separation; amino acids;
D O I
10.1016/S0021-9673(99)00889-4
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
The direct and indirect stereochemical resolution of the enantiomers of ring- and alpha-methyl-substituted phenylalanines and phenylalanine amides was attempted by high-performance liquid chromatographic methods. The direct separation was carried out on two chiral stationary phases, the crown-ether-based Crownpak CR(+), and the teicoplanin-based Chirobiotic T, while the indirect resolution was performed by applying pre-column derivatization with 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate (GITC) and N alpha-(2,4-dinitro-5-fluorophenyl)-L-alanine amide (Marfey's reagent, FDAA). The Chirobiotic T column was efficient in the separation of ring- and alpha-methyl-substituted phenylalanine analogues, but was ineffective for the amides of these analogues. The Crownpak CR(+) column separated the ring-substituted phenylalanines and amides, whereas the alpha-methylated analogues were coeluted. Of the two indirect methods, GITC derivatization seemed more effective than FDAA derivatization. (C) 2000 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:105 / 113
页数:9
相关论文
共 30 条
[1]   COVALENTLY BONDED TEICOPLANIN CHIRAL STATIONARY-PHASE FOR HPLC ENANTIOSEPARATIONS [J].
ARMSTRONG, DW ;
LIU, YB ;
EKBORGOTT, KH .
CHIRALITY, 1995, 7 (06) :474-497
[2]   DIRECT LIQUID-CHROMATOGRAPHIC SEPARATION OF RACEMATES WITH AN ALPHA-CYCLODEXTRIN BONDED PHASE [J].
ARMSTRONG, DW ;
YANG, XF ;
HAN, SM ;
MENGES, RA .
ANALYTICAL CHEMISTRY, 1987, 59 (21) :2594-2596
[3]   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
[4]   CONFORMATIONAL STUDIES ON ALAMETHICIN [J].
BURGESS, AW ;
LEACH, SJ .
BIOPOLYMERS, 1973, 12 (12) :2691-2712
[5]   ENANTIOSELECTIVE CONSTRUCTION OF A QUATERNARY ASYMMETRIC CARBON CENTER - A VERSATILE SYNTHESIS OF ALPHA-ALKYL ALPHA-AMINO-ACIDS [J].
IHARA, M ;
TAKAHASHI, M ;
NIITSUMA, H ;
TANIGUCHI, N ;
YASUI, K ;
FUKUMOTO, K .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (23) :5413-5415
[6]   CONFORMATIONAL-CHANGES OF ALAMETHICIN INDUCED BY SOLVENT AND TEMPERATURE - C-13-NMR AND CIRCULAR-DICHROISM STUDY [J].
JUNG, G ;
DUBISCHAR, N ;
LEIBFRITZ, D .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1975, 54 (02) :395-409
[7]  
KAMPHUIS J, 1992, ANN NY ACAD SCI, V672, P510
[8]   SYNTHESIS OF ALPHA,ALPHA-DISUBSTITUTED ALPHA-AMINO-ACID AMIDES BY PHASE-TRANSFER CATALYZED ALKYLATION [J].
KAPTEIN, B ;
BOESTEN, WHJ ;
BROXTERMAN, QB ;
SCHOEMAKER, HE ;
KAMPHUIS, J .
TETRAHEDRON LETTERS, 1992, 33 (40) :6007-6010
[9]   SYNTHESIS OF OPTICALLY PURE ALPHA-ALKYLATED ALPHA-AMINO-ACIDS AND A SINGLE-STEP METHOD FOR ENANTIOMERIC EXCESS DETERMINATION [J].
KRUIZINGA, WH ;
BOLSTER, J ;
KELLOGG, RM ;
KAMPHUIS, J ;
BOESTEN, WHJ ;
MEIJER, EM ;
SCHOEMAKER, HE .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1826-1827
[10]  
LEIBFRITZ D, 1989, LIEBIGS ANN CHEM, V1, P1017