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

• TODOROKI Kenichiro

  School of Pharmaceutical Sciences, University of Shizuoka

• NAKAMURA Misuzu

  School of Pharmaceutical Sciences, University of Shizuoka

• SATO Yuhi

  School of Pharmaceutical Sciences, University of Shizuoka

• GOTO Kanoko

  School of Pharmaceutical Sciences, University of Shizuoka

• NAKANO Tatsuki

  School of Pharmaceutical Sciences, University of Shizuoka

• ISHII Yasuhiro

  School of Pharmaceutical Sciences, University of Shizuoka

• MIN Jun Zhe

  School of Pharmaceutical Sciences, University of Shizuoka

• INOUE Koichi

  School of Pharmaceutical Sciences, University of Shizuoka

• TOYO’OKA Toshimasa

  School of Pharmaceutical Sciences, University of Shizuoka

Abstract

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.

Journal

• CHROMATOGRAPHY

  CHROMATOGRAPHY 37 (1), 23-28, 2016

  The Society for Chromatographic Sciences

Keywords

• DMT-MM
• D- and L-Amino acid
• Chiral derivatization
• Enantioseparation enhancer<i> </i>

Details

• CRID: 1390001205745207680
• NII Article ID: 130005133694
• NII Book ID: AA1137755X
• DOI: 10.15583/jpchrom.2015.037
• ISSN: 13483315
• ISSN: 13428284
• NDL BIB ID: 027127399
• Web Site: http://id.ndl.go.jp/bib/027127399
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I027127399
• Web Site: https://www.jstage.jst.go.jp/article/jpchrom/37/1/37_2015.037/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed