Characteristic fragmentation of bacteriohopanepolyols during atmospheric pressure chemical ionisation liquid chromatography/ion trap mass spectrometry

Helen M. Talbot*, Roger Summons, Linda Jahnke, Paul Farrimond

*Corresponding author for this work

    Research output: Contribution to journalArticle

    70 Citations (Scopus)

    Abstract

    Bacteriohopanepolyols (BHPs) fragment via characteristic pathways during atmospheric pressure chemical ionisation liquid chromatography/ion trap mass spectrometry (APCI-LC/MSn). Comparison of the MS2 spectra of bacteriohopane-32,33,34,35-tetrol (BHT) and 2β -methylbacteriohopane-32,33,34,35-tetrol has confirmed the previously proposed ring-C cleavage occurring between C-9 and 11 and C-8 and 14. This fragmentation, diagnostic of all hopanoids, also occurs in BHPs containing an amino group (-NH2) at C-35 although the higher relative stability of the ion limits this fragmentation to a minor process after protonation of the basic nitrogen function. Studies of a number of cell cultures including a prochlorophyte (Prochlorothrix hollandica) and a cyanobacterium (Chlorogloeopsis LA) demonstrate the power of this technique to detect composite BHPs with a complex biological functionality at C-35. We also report the first observation of intact pentafunctionalised bacteriohopanepolyols using this method.

    Original languageEnglish
    Pages (from-to)2788-2796
    Number of pages9
    JournalRapid Communications in Mass Spectrometry
    Volume17
    Issue number24
    Publication statusPublished - 2003

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