Negative-ion electrospray ionization mass spectrometry of N-benzyloxycarbonyl-protected 1-substituted and cyclic taurines

Jiaxi Xu, Yuan Ma, Shu Xu, Yufen Zhao

    Research output: Contribution to journalArticlepeer-review

    4 Citations (Scopus)

    Abstract

    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.

    Original languageEnglish
    Pages (from-to)1835-1838
    Number of pages4
    JournalRapid Communications in Mass Spectrometry
    Volume19
    Issue number13
    DOIs
    Publication statusPublished - 2005 Jul 11

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Spectroscopy
    • Organic Chemistry

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