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
N1 - Funding Information:
This work was partly supported by MEXT KAKENHI Grant Number 25108006 and JSPS KAKENHI Grant Number 25293007, Japan. The authors thank Shiseido Co., Ltd., (Tokyo, Japan) and Chiral Technologies Europe (Illkirch, France) for their technical support.
Publisher Copyright:
© 2015 Elsevier B.V.
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
SN - 0731-7085
VL - 116
SP - 71
EP - 79
JO - Journal of Pharmaceutical and Biomedical Analysis
JF - Journal of Pharmaceutical and Biomedical Analysis
ER -