Direct high-performance liquid chromatographic enantioseparation of free α-, β- and γ-aminophosphonic acids employing cinchona-based chiral zwitterionic ion exchangers

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• 作者：Andrea F. G. Gargano ; Michal Kohout…
• 关键词：High ; performance liquid chromatography ; Cinchona ; based chiral zwitterionic ion exchanger ; Enantiomer separation ; Chiral stationary phases ; Aminophosphonic acids ; Aminophosphinic acids
• 刊名：Analytical and Bioanalytical Chemistry
• 出版年：2013
• 出版时间：October 2013
• 年：2013
• 卷：405
• 期：25
• 页码：8027-8038
• 全文大小：751KB
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• 作者单位：Andrea F. G. Gargano (1)
  Michal Kohout (1) (2)
  Pavla Macíková (1) (3)
  Michael L?mmerhofer (4)
  Wolfgang Lindner (1)
  
  1. Department of Analytical Chemistry, University of Vienna, Waehringer Strasse 38, 1090, Vienna, Austria
  2. Department of Organic Chemistry, Institute of Chemical Technology, Technická 5, 16628, Prague, Czech Republic
  3. Regional Centre of Advanced Technologies and Materials, Department of Analytical Chemistry, Faculty of Science, Palacky University, 17. listopadu 1192/12, 77146, Olomouc, Czech Republic
  4. Institute of Pharmaceutical Sciences, University of Tübingen, Auf der Morgenstelle 8, 72076, Tübingen, Germany
  
• ISSN：1618-2650

文摘

We report a chiral high-performance liquid chromatographic enantioseparation method for free α-aminophosphonic, β-aminophosphonic, and γ-aminophosphonic acids, aminohydroxyphosphonic acids, and aromatic aminophosphinic acids with different substitution patterns. Enantioseparation of these synthons was achieved by means of high-performance liquid chromatography on CHIRALPAK ZWIX(+) and ZWIX(-) (cinchona-based chiral zwitterionic ion exchangers) under polar organic chromatographic elution conditions. Mobile phase characteristics such as acid-to-base ratio, type of counterion, and solvent composition were systematically varied in order to investigate their effect on the separation performance and to achieve optimal separation conditions for the set of analytes. Under the optimized conditions, 32 of 37 racemic aminophosphonic acids studied reached baseline separation when we employed a single generic mass-spectrometry-compatible mobile phase, with reversal of the elution order when we used (+) and (-) versions of the chiral stationary phase. Figure New zwitterionic ion-exchangers can separate free amino phosphonic acids and a change from Chiralpak ZWIX(+) to ZWIX(-) allows reversal of enantiomer elution order