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

Tsubasa Oyama, Eiichi Negishi, Hirohisa Onigahara, Nao Kusano, Yurika Miyoshi, Masashi Mita, Manabu Nakazono, Sumio Ohtsuki, Akio Ojida, Wolfgang Lindner, Kenji Hamase

Research output: Contribution to journalArticle

6 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)71-79
Number of pages9
JournalJournal of Pharmaceutical and Biomedical Analysis
Volume116
DOIs
Publication statusPublished - Dec 10 2015

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Fluorescence
Amino Acids
4-Quinolones
Electrospray ionization
Enantiomers
Fluorophores
Mass spectrometers
Protons
High Pressure Liquid Chromatography
6-methoxy-4-quinolone
Derivatives
Detectors
Injections
Temperature

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmaceutical Science
  • Drug Discovery
  • Spectroscopy
  • Clinical Biochemistry

Cite this

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. / Oyama, Tsubasa; Negishi, Eiichi; Onigahara, Hirohisa; Kusano, Nao; Miyoshi, Yurika; Mita, Masashi; Nakazono, Manabu; Ohtsuki, Sumio; Ojida, Akio; Lindner, Wolfgang; Hamase, Kenji.

In: Journal of Pharmaceutical and Biomedical Analysis, Vol. 116, 10.12.2015, p. 71-79.

Research output: Contribution to journalArticle

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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.",
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AU - Negishi, Eiichi

AU - Onigahara, Hirohisa

AU - Kusano, Nao

AU - Miyoshi, Yurika

AU - Mita, Masashi

AU - Nakazono, Manabu

AU - Ohtsuki, Sumio

AU - Ojida, Akio

AU - Lindner, Wolfgang

AU - Hamase, Kenji

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