Gas-phase reactivity of glycosides and methyl glycosides with Cu

⁺, Ag⁺ and Pb²⁺ ions by fast-atom bombardment and tandem mass spectrometry

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Eur. J. Mass Spectrom. 7, 321 - 330 (2001)

Gas-phase reactivity of glycosides and methyl glycosides with Cu⁺, Ag⁺ and Pb²⁺ ions by fast-atom bombardment and tandem mass spectrometry

Jean-Yves Salpin, Laurence Boutreau, Violette Haldys and Jeanine Tortajada^*
Laboratoire Analyse et Environnement, UMR 8587, Institut des Sciences, Université Evry Val dEssonne, Boulevard François Mitterrand, 91025 Evry Cedex, France

ABSTRACT:

The analytical potential of the complexation of three isomeric monosaccharides (D-glucose, D-galactose, D-fructose) and two methyl glycosides (O-methyl-a-D-glucose and O-methyl-b-D-glucose) by three metal ions, Ag⁺, Cu⁺ and Pb²⁺, has been investigated by fast-atom bombardment (FAB) ionization and tandem mass spectrometry. Our results have shown that the unimolecular reactivity of Ag⁺ complexes allows the characterization of the C(4) stereochemistry of the pyranose ring, whereas a distinction between D-glucose and D-fructose is not achieved. On the other hand, each of the three [Cu + monosaccharide]⁺ complexes exhibits specific dissociation patterns. We have also observed that Pb²⁺ ions induce the richest reactivity and are of particular interest for the identification of the three isomers. Finally, this study has demonstrated that the stereochemistry of the anomeric center of O-methyl-D-glucose is easily determined by reaction with Ag⁺ or Pb²⁺ ions. Several mechanisms are proposed to account for the main fragmentations of cationized glucose.

Keywords: mass spectrometry, fast-atom bombardment, cationization, silver, copper, lead, glycoside, gas-phase, unimolecular reactivity

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