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KMID : 1059519920360060879
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Journal of the Korean Chemical Society
1992 Volume.36 No. 6 p.879 ~ p.888
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Optical Resolution of Free Amino Acids with Addition of Copper(Ⅱ) Chelates in a Reversed-Phase Liquid Chromatography
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Lee Sun-Haing
Oh Tae-Sub
An Hong-Yeup
Park Kyung-Sug
Oh Sang-Oh
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Abstract
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Separation of the optical isomers of free amino acids by a reversed phase high performance liquid chromatography has been studied by adding a copper(Ⅱ) complex of L-proline or L-proline derivatives (hydroxy-L-proline, N-benzyl-L-proline, p-xylenyl-L-proline, p-xylenyl-hydroxy-L-proline) in the mobile phase. An OPA postcolumn detection system was used for the detection of amino acids. The chromatographic properties for the free amino acids were discussed in terms of the pH, the kinds and concentration of chelate or organic modifier. The retention behaviors of the free amino acids were considerably different from, those of DNS-amino acids or DABS-amino acids. The enantioselectivity of the free amino acids was better than that of derivatized amino acids. The enantioselectivity between the optical isomers observed by use of the Cu(Ⅱ)-p-xylenyl-L-proline chiral cheleate was the best among the several copper(Ⅱ) chelate. A separation mechanism could be illustrated not only by the hydrophobic interaction of the diastereomer with stationary phase but also by the steric effect of the ligand exchange reaction between the free-amino acids and copper chelate.
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