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Chiral stationary phase covalently bound with a chiral pseudo‐18‐crown‐6 ether for enantiomer separation of amino compounds using a normal mobile phase
Author(s) -
Hirose Keiji,
Yongzhu Jin,
Nakamura Takashi,
Nishioka Ryota,
Ueshige Tetsuro,
Tobe Yoshito
Publication year - 2005
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20138
Subject(s) - enantiomer , chemistry , chiral derivatizing agent , crown ether , chiral column chromatography , high performance liquid chromatography , amino acid , chromatography , selectivity , chiral resolution , silica gel , phase (matter) , organic chemistry , catalysis , ion , biochemistry
In order to apply the excellent chiral recognition ability of chiral pseudo‐18‐crown‐6 ethers that we developed to chiral separation, we prepared a chiral stationary phase (CSP) by immobilizing a chiral pseudo‐18‐crown‐6‐type host on 3‐aminopropyl silica gel. A chiral column was prepared by the slurry‐packing method in a stainless steel HPLC column. A liquid chromatography system using this CSP combined with the detection by mass spectrometry was used for enantiomer separation of amino compounds. A normal mobile phase can be used on this CSP as opposed to conventional dynamic coating‐type CSPs. Enantiomers of 18 common natural amino acids were efficiently separated. The chiral separation observed for amino acid methyl esters, amino alcohols, and lipophilic amines was fair using this HPLC system. In view of the correlation between the enantiomer selectivity observed in chromatography and the complexion in solution, the chiral recognition in host–guest interactions might contribute to this enantiomer separation. Chirality 17:142–148, 2005. © 2005 Wiley‐Liss, Inc.