ガスクロマトグラフィーによるアミン及びアミノ酸光学異性体分離用の新しい固定相としてのトリペプチドエステルのs-トリアジン誘導体

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It is well known that N-acyl dipeptide esters are the useful optically active stationary phases for gas chromatographic separation of amino acid enantiomers, but N-acyl tripeptide esters give only smaller separation factors compared with the corresponding N-acyl dipeptide ester phases although tripeptide derivatives contain a longer peptide chain than dipeptide derivatives. In order to investigate the effect of extending the peptide chain in optically active stationary phases containing a s-triazine ring, we prepared the new s-triazine derivative of tripeptide ester, N,N'-[2,4-(6-ethoxy-1,3,5-triazine)diyl]-bis-(L-valyl-L-valyl-L-valine isopropyl ester) [I]. It was found that this new compound has more excellent property in relation to enantiomer separation (amino acid and amine) compared with the corresponding s-triazine derivative of dipeptide ester, N,N'-[2,4-(6-ethoxy-1,3,5-triazine) diyl]-bis-(L-valyl-L-valine isopropyl ester) [II]. For example, the separation factors for N-TFAD-L-methionine isopropyl ester are 1.089 on [I] and 1.029 on [II] at 150℃, and for N-TFA-dl-α-(1-naphthyl)ethylamine are 1.072 on [I] and 1.044 on [II] at 160℃. On the other hand, the maximum permissible operating temperature of this new stationary phase with an open tubular glass column (about 200℃) is considerablly higher than those of all published optically active stationary phases. For example, in the isothermal mode at 200℃. N,N'-di-PFP-DL-lysine isopropyl ester was separated within 15 min on a 34 m column.
社団法人日本分析化学会の論文
1979-02-05

ガスクロマトグラフィーによるアミン及びアミノ酸光学異性体分離用の新しい固定相としてのトリペプチドエステルのs-トリアジン誘導体

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