Synthesis of benzofurazan derivatization reagents for carboxylic acids in liquid chromatography/electrospray ionization-tandem mass spectrometry.
The applicability of benzofurazan derivatization regents to carboxylic acids analysis in LC/ESI-MS/MS (high-performance liquid chromatography/electrospray ionization tandem mass spectrometry) was examined. The product ion spectra of DAABD-AE {4-[2-(N,N-dimethylamino)ethylaminosulfonyl]-7-(2-aminoethylamino)-2,1,3-benzoxadiazole}, DAABD-PZ {4-[2-(N,N-dimethylamino)ethylaminosulfonyl]-7-N-piperazino-2,1,3-benzoxadiazole}, DAABD-PiCZ {4-[4-carbazoylpiperidin-1-yl]-7-[2-(N,N-dimethylamino)ethylaminosulfonyl]-2,1,3-benzoxadiazole}, DAABD-ProCZ {4-[2-carbazoylpyrrolidin-1-yl]-7-[2-(N,N-dimethylamino) ethylaminosulfonyl]-2,1,3-benzoxadiazole} and DAABD-Apy {4-[2-(N,N-dimethylamino)ethylaminosulfonyl]-7-(3-aminopyrrolidin-1-yl)-2,1,3-benzoxadiazole}, and their acetylated compounds were obtained. An intense fragment ion at m/z 151 corresponding to (dimethylamino)ethylaminosulfonyl moiety was observed in each spectra, suggesting that these reagents were suitable for ESI-MS/MS analysis. DAABD-AE, DAABD-APy and DAABD-PZ were applied to the analysis of octanoic acid and it was found that DAABD-AE and DAABD-APy gave high signal intensity suitable for LC/ESI-MS/MS.
Santa
Tomofumi
T
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, Japan. santa@mol.f.u-tokyo.ac.jp
Al-Dirbashi
Osama Y
OY
Ichibangase
Tomoko
T
Fukushima
Takeshi
T
Rashed
Mohamed S
MS
Funatsu
Takashi
T
Imai
Kazuhiro
K
D001583:Benzoxazoles / Q000737:chemistry; D002264:Carboxylic Acids / Q000032:analysis / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D007202:Indicators and Reagents / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification*; D012680:Sensitivity and Specificity; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification*; D053719:Tandem Mass Spectrometry / Q000379:methods*
C507985:4-(2-(N,N-dimethylamino)ethylaminosulfonyl)-7-(2-aminoethylamino)-2,1,3-benzoxadiazole; D001583:Benzoxazoles; D002264:Carboxylic Acids; D007202:Indicators and Reagents; D010069:Oxadiazoles; D013449:Sulfonamides; C020160:benzofurazan