In situ formation of C-glycosides during electrospray ionization tandem mass spectrometry of a series of synthetic amphiphilic cholesteryl polyethoxy neoglycolipids containing N-acetyl-D-glucosamine

  • Joseph Banoub
  • Paul Boullanger
  • Dominique Lafont
  • Alejandro Cohen
  • Anas El Aneed
  • Elizabeth Rowlands
Short Communication


In this communication, the structural analysis of six synthetic O-Linked amphiphilic cholesteryl polyethoxy neoglycolipids containing N-acetyl-D-glucosamine was performed by electrospray ionization mass spectrometry in the positive ion mode, with a QqTOF-MS/MS hybrid instrument. The MS/MS analyses provided evidence for the “in situ” formation, in the collision cell of the tandem mass spectrometer, of an unexpected and unique [C-glycoside]+ product ion, resulting from an ion-molecule reaction between the N-acetyl-D-glucosamine oxonium ion and the neutral cholesta-3,5-diene molecule. Quasi MS3 analysis of this ion resulted in the dissociation of the precursor [C-glycoside]+ ion, which produced the expected third generation N-acetyl-D-glucosamine oxonium and the protonated cholesta-3,5-diene product ions.


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Copyright information

© American Society for Mass Spectrometry 2005

Authors and Affiliations

  • Joseph Banoub
    • 1
    • 4
  • Paul Boullanger
    • 3
  • Dominique Lafont
    • 3
  • Alejandro Cohen
    • 4
  • Anas El Aneed
    • 4
  • Elizabeth Rowlands
    • 4
  1. 1.Special Projects, Science BranchDepartment of Fisheries and OceansSt. John’sCanada
  2. 2.Northwest Atlantic Fisheries Center, Fisheries and Oceans CanadaMemorial University of NewfoundlandSt. John’sCanada
  3. 3.Laboratoire de Chimie Organique 2Université Claude BernardVilleurbanneFrance
  4. 4.Biochemistry DepartmentMemorial University of NewfoundlandSt. John’sCanada

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