Tandem mass spectra of ammonium adducts of monosaccharides: differentiation of diastereomers

Abstract

Tandem mass spectra of ammonium adducts of monosaccharides gave characteristic fragmentation patterns involving elimination of NH3/H2O followed by multiple eliminations of H2O and cross ring cleavages. Tandem mass spectra were examined over a range of collision energies (1-20 eV) on a triple-quadrupole mass spectrometer. The breakdown behavior of the ammonium adducts revealed patterns that could differentiate diastereomers of monosaccharides.

Characterization of Protonated Model Disaccharides from Tandem Mass Spectrometry and Chemical Dynamics Simulations

“…This mechanism has been proposed in many studies andi ss upported by isotope-labeling experiments. [38] The second mechanism, which implies the elimination of ah ydrogen atom attached to an adjacent carbon atom and leads to the formation of adouble bond, [36d, 39] corresponds to what is observedi nt he presents imulations. The first step observed here for the formation of m/z 368 was indeed the cleavage of aC ÀO(H) bond.…”

Molecular identification in metabolomics using infrared ion spectroscopy

“…Indeed, for the definitive identification of ManNAc from patient body fluids, it was necessary to use NMR techniques requiring significantly larger sample volumes and having significantly lower sensitivity than MS-based methods 8 . Previous studies have demonstrated the ability to distinguish monosaccharides using MS alone, but have mainly relied on either following complex MS >2 dissociation channels, often based only on differences in the relative peak intensities of common fragmentation channels 9–11 , or derivatization schemes that are difficult to apply to complex biological samples 12, 13 .…”

Diastereomeric differentiation of two pairs of glycal derivatives by electrospray ionization tandem mass spectrometry

“…5 Madhusudanan et al have reported CID-MS/MS studies of the ammonium adducts of hexoses and the fragmentation patterns were used to differentiate diastereomers of monosasccharides. 6 Salpin and Tortajada have reported an electrospray ionization/tandem mass spectrometric study of hexoses and pentoses using lead cationization. 7 Recently, Zhu and Sato reported the distinction of underivatized monosaccharides using ESI-MS n of their ammonium adducts.…”