Liquid chromatographic enantioseparations on crown ether-based chiral stationary phases

被引：78
作者：
Hyun, Myung Ho [1 ,2 ]
机构：
[1] Pusan Natl Univ, Dept Chem, Busan 609735, South Korea
[2] Pusan Natl Univ, Chem Inst Funct Mat, Busan 609735, South Korea
来源：
JOURNAL OF CHROMATOGRAPHY A | 2016年 / 1467卷
关键词：
Chiral crown ether; Chiral stationary phase; Enantiomer separation; Liquid chromatography; BETA-AMINO ACIDS; HOST-GUEST COMPLEXATION; (+)-(18-CROWN-6)-2,3,11,12-TETRACARBOXYLIC ACID; DIRECT RESOLUTION; CAPILLARY-ELECTROPHORESIS; ENANTIOMERIC SEPARATION; OPTICAL RESOLUTION; NMR DISCRIMINATION; RACEMIC AMINES; ANALOGS;
D O I：
10.1016/j.chroma.2016.07.049
中图分类号：
Q5 [生物化学];
学科分类号：
071010 ; 081704 ;
摘要：
Various liquid chromatographic chiral stationary phases (CSPs) have been developed for the resolution of racemic compounds. In particular, CSPs based on chiral crown ethers have been known to be useful in the resolution of racemic compounds containing a primary amino group. In this paper, the development of two types of CSPs based on the chiral crown ethers containing 1,1'-binaphthyl unit(s) or tartaric acid units as chiral barrier(s) and their applications to the resolution of various racemic compounds were reviewed. The structural characteristics of eleven CSPs and their chromatographic behaviors for the resolution of racemic primary amino and non-primary amino compounds were included. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码：19 / 32
页数：14
相关论文
共 92 条
  • [1] AboulEnein HY, 1997, BIOMED CHROMATOGR, V11, P7, DOI 10.1002/(SICI)1099-0801(199701)11:1<7::AID-BMC607>3.0.CO
  • [2] 2-F
  • [3] DIRECT CHIRAL LIQUID-CHROMATOGRAPHIC SEPARATION OF TOCAINIDE ENANTIOMERS ON A CROWNPAK (CR) COLUMN AND ITS APPLICATION TO PHARMACEUTICAL FORMULATIONS AND BIOLOGICAL-FLUIDS
    ABOULENEIN, HY
    BAKR, SA
    ISLAM, MR
    ROTHCHILD, R
    [J]. JOURNAL OF LIQUID CHROMATOGRAPHY, 1991, 14 (19): : 3475 - 3481
  • [4] Liquid Chromatographic Resolution of Amino Acid Esters of Acyclovir Including Racemic Valacyclovir on Crown Ether-Based Chiral Stationary Phases
    Ahn, Seong Ae
    Hyun, Myung Ho
    [J]. CHIRALITY, 2015, 27 (03) : 268 - 273
  • [5] DIRECT RESOLUTION OF ENANTIOMERS BY LIQUID AFFINITY-CHROMATOGRAPHY ON ALBUMIN-AGAROSE UNDER ISOCRATIC CONDITIONS
    ALLENMARK, S
    BOMGREN, B
    BOREN, H
    [J]. JOURNAL OF CHROMATOGRAPHY, 1982, 237 (03): : 473 - 477
  • [6] Chiral recognition of (18-crown-6)-tetracarboxylic acid as a chiral selector determined by NMR spectroscopy
    Bang, EJ
    Jung, JW
    Lee, WJ
    Lee, DW
    Lee, WT
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (09): : 1685 - 1692
  • [7] Comparison of Chiral Separations of Aminophosphonic Acids and Their Aminocarboxylic Acid Analogs Using a Crown Ether Column
    Barnhart, Wesley W.
    Xia, Xiaoyang
    Jensen, Randy
    Gahm, Kyung H.
    [J]. CHIRALITY, 2013, 25 (07) : 369 - 378
  • [8] MOLECULAR RECEPTORS - FUNCTIONALIZED AND CHIRAL MACROCYCLIC POLYETHERS DERIVED FROM TARTARIC ACID
    BEHR, JP
    GIRODEAU, JM
    HAYWARD, RC
    LEHN, JM
    SAUVAGE, JP
    [J]. HELVETICA CHIMICA ACTA, 1980, 63 (07) : 2096 - 2111
  • [9] High-performance liquid chromatographic enantioseparation of β-3-homo-amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase
    Berkecz, Robert
    Ilisz, Istvan
    Fueloep, Ferenc
    Pataj, Zoltan
    Hyun, Myung Ho
    Peter, Antal
    [J]. JOURNAL OF CHROMATOGRAPHY A, 2008, 1189 (1-2) : 285 - 291
  • [10] High-performance liquid chromatographic enantioseparation of β-amino acid stereoisomers on a (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid-based chiral stationary phase
    Berkecz, Robert
    Sztojkov-Ivanov, Anita
    Ilisz, Istvan
    Forro, Eniko
    Fulop, Ferenc
    Hyun, Myung Ho
    Peter, Antal
    [J]. JOURNAL OF CHROMATOGRAPHY A, 2006, 1125 (01) : 138 - 143
12345678910