1. Design and synthesis of a novel pre-column derivatization reagent with a 6-methoxy-4-quinolone moiety for fluorescence and tandem mass spectrometric detection and its application to chiral amino acid analysis
- Author
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Nao Kusano, Akio Ojida, Yurika Miyoshi, Masashi Mita, Wolfgang Lindner, Sumio Ohtsuki, Tsubasa Oyama, Eiichi Negishi, Manabu Nakazono, Kenji Hamase, and Hirohisa Onigahara
- Subjects
Male ,Electrospray ionization ,Clinical Biochemistry ,Pharmaceutical Science ,Quinolones ,Mass spectrometry ,Fluorescence ,Analytical Chemistry ,Mice ,chemistry.chemical_compound ,Tandem Mass Spectrometry ,Drug Discovery ,Animals ,Moiety ,Amino Acids ,Derivatization ,Spectroscopy ,Fluorescent Dyes ,chemistry.chemical_classification ,Chromatography ,Enantioselective synthesis ,Stereoisomerism ,Amino acid ,Mice, Inbred C57BL ,chemistry ,Drug Design ,Reagent ,Enantiomer - Abstract
A new pre-column derivatization reagent with a 6-methoxy-4-quinolone (6-MOQ) moiety for amino acid analysis, 2,5-dioxopyrrolidin-1-yl(2-(6-methoxy-4-oxoquinolin-1(4H)-yl)ethyl) carbonate (6-MOQ-EtOCOOSu), was designed and synthesized. 6-MOQ is a thermo/photostable fluorophore with a high proton-affinity site and sensitive determination could be carried out by a fluorescence detector and also by an electrospray ionization mass spectrometer. Derivatization of amino acids with 6-MOQ-EtOCOOSu was completed within 1 min under mild basic conditions at room temperature. The 6-MOQ derivatives of all chiral proteinogenic amino acids were separated using the combination of three enantioselective columns, Chiralpak QN-AX, Chiralpak ZXIX(+), and KSAACSP-001S, with separation factors of higher than 1.07. The present reagent enables the sensitive determination of amino acid enantiomers, and the values of LLOD using a chiral-HPLC-MS/MS system were 0.05-50 fmol/injection.
- Published
- 2015
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