Preparation and evaluation of a chiral stationary phase covalently bound with a chiral pseudo-18-crown-6 ether having a phenolic hydroxy group for enantiomer separation of amino compounds.

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  • Additional Information
    • Source:
      Publisher: Elsevier Country of Publication: Netherlands NLM ID: 9318488 Publication Model: Print-Electronic Cited Medium: Print ISSN: 0021-9673 (Print) Linking ISSN: 00219673 NLM ISO Abbreviation: J Chromatogr A Subsets: MEDLINE
    • Publication Information:
      Original Publication: Amsterdam ; New York : Elsevier, 1993-
    • Subject Terms:
      Amines/*isolation & purification ; Amino Acids/*isolation & purification ; Amino Alcohols/*isolation & purification ; Chromatography, High Pressure Liquid/*methods ; Crown Ethers/*chemistry; Amines/chemistry ; Amino Acids/chemistry ; Amino Alcohols/chemistry ; Chromatography, High Pressure Liquid/instrumentation ; Magnetic Resonance Spectroscopy/methods ; Molecular Structure ; Reproducibility of Results ; Stereoisomerism
    • Abstract:
      In order to develop a chiral stationary phase (CSP), which has even higher separation ability than the corresponding commercially available crown ether based CSP (OA-8000 having a pseudo-18-crown-6 ether with an OMe group as a selector), chemically bonded type CSP having a phenolic OH group on a crown ring was developed. Normal mobile phases with or without acid additive can be used with this OH type CSP in contrast to the conventional OMe type CSP which has a neutral chiral selector. Enantiomers of 25 out of 27 amino compounds, including 20 amino acids, 5 amino alcohols, and 2 lipophilic amines, were efficiently separated on a column with this CSP. Nine amino compounds out of 27 were separated with better separation factors than the corresponding OMe type CSP. It is noteworthy that the chromatography on this CSP exhibited excellent enantiomer-separations for amines and amino alcohols when triethyl amine was used as an additive in the mobile phase. Comparison of enantiomer separation ability on this OH type of CSP and on the OMe type of CSP and correlation between the enantioselectivity in chiral chromatography and that of the corresponding model compounds in solution imply that the chiral separation arose from chiral recognition in host guest interactions.
    • Accession Number:
      0 (Amines)
      0 (Amino Acids)
      0 (Amino Alcohols)
      0 (Crown Ethers)
      63J177NC5B (18-crown-6)
    • Publication Date:
      Date Created: 20060729 Date Completed: 20061122 Latest Revision: 20121115
    • Publication Date:
      20231215
    • Accession Number:
      10.1016/j.chroma.2006.07.003
    • Accession Number:
      16872621