ガスクロマトグラフィーによるアミノ酸光学異性体分離用の新しい固定相としてのL-リジンアミドのs-トリアジン誘導

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Although s-triazine derivatives of amino acid esters, dipeptide esters and tripeptide esters are very valuable as the thermostable optically active stationary phases for the gas chromatographic separation of amino acid enantiomers, their resolving power is rather unsatisfactory. To improve such property, a new s-triazine derivative of the amino acid amide, N, N', N"-[2, 4, 6-(1,3,5-triazine) triyl] tris (N^α-1auroyl-L-1ysine-t-butyl-amide) (I) was synthesized. Several N-TFA-DL-amino acid isopropyl esters were resolved with good separation factors on a glass capillary column (0.25 mm i. d.×40 m) coated with the compound (I). In relation to the separation of amino acid enantiomers, this new compound (I) has more excellent property than the typical s-triazine derivatives of amino acid ester, dipeptide ester and tripeptide ester such as N, N', N"-[2,4,6-(1,3,5-triazine)triyl] tris(L-valine isopropyl ester) (II), N, N'-[2, 4-(6-ethoxy-1,3,5-tri-azine)diyl] bis(L-valyl-L-valine isopropyl ester) (III) and N, N'-[2,4-(6-ethoxy-1,3,5-triazine)diyl] bis(L-valyl-L-valyl-L-valine isopropyl ester) (IV), which were already reported by the authors. For example, the separation factors for N-TFA-DL-valine isopropyl ester are 1.114 on (I), 1.047 on (II), and 1.055 on (III) at 110℃, and for N-TFA-DL-methionine isopropyl ester are 1.105 on (I), 1.000 on (II), 1.029 on (III) and 1.089 on (IV) at 150℃. The high separation factors on (I) allow the separation of some amino acid enantiomers with a packed column [10 % coated on Shimalite W { (170〜200) mesh}, 0.5mm i. d.×2.8m]. This compound (I) shows rather high thermal stability, and its maximum permissible operational temperature is about 150℃. Moreover, due to its relative low melting point { (93-95)℃}, the column is effective over a wide range of temperature. It is concluded that this new compound (I) is very available as an optically active stationary phase for gas chromatographic separation of amino acid enantiomers.
社団法人日本分析化学会の論文
1980-04-05

ガスクロマトグラフィーによるアミノ酸光学異性体分離用の新しい固定相としてのL-リジンアミドのs-トリアジン誘導

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