Enantioseparation and chiral recognition of α-amino acids and their derivatives on (?-18-crown-6-tetracarboxylic acid bonded silica by capillary electrochromatography

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• 作者：Enqi Wu ; Kyung Tae Kim ; Sreenivas Kalyan Adidi…
• 关键词：Enantioseparation ; Amino acid ; (? ; 18 ; Crown ; 6 ; 2 ; 3 ; 11 ; 12 ; tetracarboxylic acid bonded silica ; Capillary electrochromatography ; Thermodynamic parameters
• 刊名：Archives of Pharmacal Research
• 出版年：2015
• 出版时间：August 2015
• 年：2015
• 卷：38
• 期：8
• 页码：1499-1505
• 全文大小：630 KB
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• 作者单位：Enqi Wu (1)
  Kyung Tae Kim (2)
  Sreenivas Kalyan Adidi (2)
  Young Keun Lee (3)
  Jong Woon Cho (2)
  Wonjae Lee (4)
  Jong Seong Kang (2)
  
  1. School of Lifescience, Inner Mongolia University for the Nationalities, Tongliao, China
  2. College of Pharmacy, Chungnam National University, Daejeon, 305-764, Korea
  3. Daejeon Health Sciences College, Daejeon, 300-711, Korea
  4. College of Pharmacy, Chosun University, Gwangju, 501-759, Korea
  
• 刊物主题：Pharmacy; Pharmacology/Toxicology;
• 出版者：Springer Netherlands
• ISSN：1976-3786

文摘

Capillary electrochromatography was employed for enantioseparation of α-amino acids and their derivatives. (?-18-Crown-6-2,3,11,12-tetracarboxylic acid bonded on the silica was used as the chiral stationary phase and methanol/Tris-citric acid (20?mM, pH 3.0-.5) (20:80, v/v) was used as mobile phase. The enantioseparation performance was discussed and structure-chiral separation relationship were tried to be explained. The enantiomeric resolution was increased when the pH of the mobile phase decreased or hydrogen of amino acid was substituted with halogen. The resolution of 4-bromophenylalanine was 2.37 at pH 4.5, however, this value was increased to 3.35 at pH 3.0. Bromo- or chloro-substituted phenylalanine tended to show higher resolution than fluoro-substituted one. For fluoro-substituted phenylalanine the resolution was increased in order of 4-, 3- and 2-substituted one. α-Methyltryptamine did not show reasonable separation. As the thermodynamic study is a useful tool to understand the chiral recognition, the temperature effect on the enantioseparation was studied and the thermodynamic parameters were calculated. The most important mechanism of chiral recognition for the analytes tested could be barrier effects based on the thermodynamic calculations. The coefficient of determination between hydrophobicity and separation factor was found to be 0.87, indicating favorable separation with higher hydrophobicity of amino acids.