TY - JOUR
T1 - 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
AU - Oyama, Tsubasa
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
PY - 2015/12/10
Y1 - 2015/12/10
N2 - 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.
AB - 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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U2 - 10.1016/j.jpba.2015.05.039
DO - 10.1016/j.jpba.2015.05.039
M3 - Article
C2 - 26166005
AN - SCOPUS:84945449704
VL - 116
SP - 71
EP - 79
JO - Journal of Pharmaceutical and Biomedical Analysis
JF - Journal of Pharmaceutical and Biomedical Analysis
SN - 0731-7085
ER -