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Laurence Boutreau, Emmanuelle Lééon,a Jean-Yves Salpin,a Badia Amekraz,b Christophe
Moulinb and Jeanine Tortajadaa*
aLaboratoire Analyse et Environnement, UMR CNRS 8587, Université d’Evry, Val
d’Essonne Bât. des Sciences, Boulevard François Mitterrand, 91025 Evry Cedex, France. E-mail jeanine.tortajada@chimie.univ-evry.fr
bCEA
SACLAY, DEN/DPC/SECR, Laboratoire de Spéciation des radionucléides et des Molécules, Bâtiment 391, 91191 Gif/Yvette Cedex, France |
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The analytical distinction of the most common isomeric underivatized hexoses was investigated by means of mass spectrometry experiments. Electrospray ionization and tandem
mass spectrometry were used in the analysis of silver and copper-coordinated monosaccharides (D-glucose, D-galactose, D-fructose, O-methyl-α-D-glucose and
O-methyl-β-D-glucose). The results show that cationization by Ag+ allows the differentiation of the three first monosaccharides while the complexes
formed by association of Cu+ with these three monosacharides display a similar reactivity that prevents stereoisomer distinction. Unlike copper, silver adduct-ions of
both α and β anomeric O-methyl-D-glucoses exhibit specific decomposition patterns (i.e. a loss of methanol for the α-anomer and a loss of silver
hydride for the β-anomer), which allow an easy characterization. A theoretical survey of selected complexes, based on the use of DFT calculations were carried out on
both anomers in order to rationalize the experimental findings. |
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Keywords:
mass spectrometry, gas phase, electrospray, cationization, silver, copper, monosaccharides, glucosides, DFT
calculations |
