Gas-phase reactivity of glycosides and methyl glycosides with Cu$^+$, Ag$^+$ and Pb$^{2+}$ ions by fast-atom bombardment and tandem mass spectrometry - Archive ouverte HAL Access content directly
Journal Articles European Journal of Mass Spectrometry Year : 2001

Gas-phase reactivity of glycosides and methyl glycosides with Cu$^+$, Ag$^+$ and Pb$^{2+}$ ions by fast-atom bombardment and tandem mass spectrometry

Abstract

The analytical potential of the complexation of three isomeric monosaccharides (D-glucose, D-galactose, D-fructose)and two methyl glycosides (O-methyl-α-D-glucose and O-methyl-β-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.
Fichier principal
Vignette du fichier
AgCuPb-hexoses_revised_HAL.pdf (279.97 Ko) Télécharger le fichier
Origin : Files produced by the author(s)

Dates and versions

hal-00068544 , version 1 (02-02-2023)

Identifiers

Cite

Jean-Yves Salpin, Laurence Boutreau, Violette Haldys, Jeanine Tortajada. Gas-phase reactivity of glycosides and methyl glycosides with Cu$^+$, Ag$^+$ and Pb$^{2+}$ ions by fast-atom bombardment and tandem mass spectrometry. European Journal of Mass Spectrometry, 2001, 7 (4-5), pp.321-330. ⟨10.1255/ejms.442⟩. ⟨hal-00068544⟩
42 View
0 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More