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

Authors

  • Helen M. Talbot,

    Corresponding author
    1. NRG, School of Civil Engineering and Geosciences, Drummond Building, University of Newcastle, Newcastle upon Tyne NE1 7RU, UK
    • NRG, School of Civil Engineering and Geosciences, Drummond Building, University of Newcastle, Newcastle upon Tyne NE1 7RU, UK.
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  • Roger Summons,

    1. Department of Earth, Atmospheric and Planetary Sciences, Massachusetts Institute of Technology, 77 Massachusetts Avenue E34-246, Cambridge, MA 02139-4307, USA
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  • Linda Jahnke,

    1. NASA Ames Research Center, Moffett Field, CA 94035, USA
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  • Paul Farrimond

    1. NRG, School of Civil Engineering and Geosciences, Drummond Building, University of Newcastle, Newcastle upon Tyne NE1 7RU, UK
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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. Copyright © 2003 John Wiley & Sons, Ltd.

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