The in situ gas-phase formation of a C-glycoside ion obtained during electrospray ionization tandem mass spectrometry. A unique intramolecular mechanism involving an ion-molecule reaction

Rapid Communications in Mass Spectrometry : RCM
Joseph H BanoubTravis D Fridgen

Abstract

This study examines the electrospray ionization mass spectrometry (ESI-MS), in-source collision-induced dissociation (CID) fragmentation and low-energy collision-induced dissociation tandem mass spectrometry (CID-MS/MS) of a synthetic pair of β- and α-anomers of the amphiphilic cholesteryl polyethoxy neoglycolipids containing the 2-azido-2-deoxy-D-galactosyl-D-GalN3 moiety. We describe the novel and unique in situ gas-phase formation of a C-glycoside ion formed during all these gas-phase processes and propose a reasonable mechanism for its formation. The synthetic amphiphilic glycolipids were composed of the 2-deoxy-2-azido-D-galactosyl moiety (GalN3, the hydrophilic part) covalently attached to a polyethoxy spacer which is covalently linked to the cholesteryl moiety (hydrophobic part). The 2-azido-2-deoxy-α- and β-D-galactosyl-containing glycolipids were studied by in-time and in-space ESI-MS and CID-MS/MS in positive ion mode, with quadrupole ion trap (QIT), quadrupole-quadrupole-time-of-flight (QqTOF), and Fourier transform ion cyclotron resonance (FTICR) instruments. Conventional single-stage ESI-MS analysis showed the formation of the protonated molecule. During the single-stage ESI-MS analysis and the CID-MS/MS of the [M+...Continue Reading

References

May 15, 2003·Angewandte Chemie·Balagurunathan KuberanRobert J Linhardt
Sep 18, 2003·Bioconjugate Chemistry·Eric PerouzelAndrew D Miller
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Sep 1, 1992·Journal of the American Society for Mass Spectrometry·S A McLuckey

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Citations

Dec 21, 2018·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Andreas FredenhagenLukas Oberer
Feb 1, 2020·Rapid Communications in Mass Spectrometry : RCM·Abanoub MikhaelJoseph Banoub

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