Negative-ion electrospray ionization mass spectrometry of N-benzyloxycarbonyl-protected 1-substituted and cyclic taurines.
The negative-ion mass spectrometric behavior of N-benzyloxycarbonyl-protected 1-substituted and cyclic taurines has been investigated under electrospray ionization conditions. Their fragmentation pathways are proposed and supported by collisionally activated dissociation product-ion spectrometry. The deprotonated substituted taurines preferentially eliminate a molecule of benzyl alcohol to yield isocyanato-sulfonate ions, which further generate alkene-2-sulfonate ions by loss of isocyanic acid. The isocyanato-sulfonate ions of 1-substituted taurines could further generate aziridine-2-sulfonate ion via ring rearrangements by loss of CO plus benzyne and carbene moieties, respectively, while the isocyanato-sulfonate ions of cyclic taurines could further give rise to cycloalkene anion radicals. An obvious substituent effect on the fragmentations of the title compounds was observed.
Xu
Jiaxi
J
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China. jxxu@pku.edu.cn
Ma
Yuan
Y
Xu
Shu
S
Zhao
Yufen
Y
D003517:Cyclopentanes / Q000138:chemical synthesis*; D008401:Gas Chromatography-Mass Spectrometry; D007202:Indicators and Reagents; D021241:Spectrometry, Mass, Electrospray Ionization; D013654:Taurine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*
D003517:Cyclopentanes; D007202:Indicators and Reagents; D013654:Taurine