title: Chiral stationary phase covalently bound with a chiral pseudo-18-crown-6 ether for enantiomer separation of amino compounds using a normal mobile phase.
abstract: 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.
authors.affiliation: Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, Osaka, Japan.
authors.forename: Keiji
authors.initials: K
authors.lastname: Hirose
authors.forename: Jin
authors.initials: J
authors.lastname: Yongzhu
authors.forename: Takashi
authors.initials: T
authors.lastname: Nakamura
authors.forename: Ryota
authors.initials: R
authors.lastname: Nishioka
authors.forename: Tetsuro
authors.initials: T
authors.lastname: Ueshige
authors.forename: Yoshito
authors.initials: Y
authors.lastname: Tobe
mesh_terms: D000596:Amino Acids / Q000737:chemistry / Q000302:isolation & purification; D000605:Amino Alcohols / Q000737:chemistry / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D002853:Chromatography, Liquid; D043844:Crown Ethers / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry*; D013058:Mass Spectrometry; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D000605:Amino Alcohols; D043844:Crown Ethers; D004988:Ethers, Cyclic; C015762:18-crown-6