Online ISSN : 1348-3315
Print ISSN : 1342-8284
ISSN-L : 1342-8284
Original papers
4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride as an Enantioseparation Enhancer for Chiral Derivatization-LC Analysis of D- and L-Amino acids
Kenichiro TODOROKIMisuzu NAKAMURAYuhi SATOKanoko GOTOTatsuki NAKANOYasuhiro ISHIIJun Zhe MINKoichi INOUEToshimasa TOYO’OKA
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2016 Volume 37 Issue 1 Pages 23-28


We have developed a high-resolution chiral derivatization-LC method for the determination of D- and L-amino acids using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as an enantioseparation enhancer. In this method, D- and L-amino acids were derivatized with (S)-(-)-1-(naphthyl)ethylamine (NEA) in the presence of DMT-MM as a condensing agent. These conditions resulted in the amino group of the D- and L-amino acid-NEA derivative being introduced in the triazine unit of DMT-MM, producing sterically bulky diastereoisomers. The resulting derivatives of the D- and L-amino acids could be discriminated and successfully enantioseparated through reversed-phase LC. This enantioseparation enhancement effect was demonstrated when using six other commercially available chiral amines as derivatization reagents. Since triazine modification possesses high ESI-responsivity, they showed higher sensitivities than non-triazine derivatives. The developed derivatization method was successfully applied to highly sensitive quantification of D- and L-amino acids by combining LC-MS/MS analysis.

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© 2016 The Society for Chromatographic Sciences
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