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Issue 29, 2018
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Collision-induced dissociation of sodiated glucose, galactose, and mannose, and the identification of anomeric configurations

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Abstract

Collision-induced dissociation of sodiated α-glucose, β-glucose, α-galactose, β-galactose, α-mannose, and β-mannose was studied using electronic structure calculations and resonance excitation in a low-pressure linear ion trap. We made an extensive search of conformers and transition states in calculations to ensure the transition state with the lowest barrier height for each dissociation channel could be located. The major dissociation channels, in addition to desodiation, are cross-ring dissociation and dehydration. Cross-ring dissociation starts with H atom transfer from the O1 atom to the O0 atom, followed by the cleavage of the C1–O0 bond. Dehydration of the anomer with O1 and O2 atoms in the cis configuration involves the transfer of an H atom from the O2 atom to the O1 atom, followed by the cleavage of the C1–O1 bond. In contrast, dehydration of the anomer with O1 and O2 atoms in the trans configuration mainly occurs through H atom transfer from the O3 or O2 atom to the O1 atom for glucose, from the O3 or O4 atom to the O1 atom for galactose, and from the O4 or O2 atom to the O1 atom for mannose, followed by the cleavage of the C1–O1 bond. The dehydration barrier heights are lower than those of cross-ring dissociation for cis anomers, but higher than those of cross-ring dissociation for trans anomers. The relative barrier heights from calculations are consistent with the experimental measurements of branching ratios. Both computational and experimental results show that the branching ratio of dehydration can be generalized as a simple rule for rapidly identifying the anomeric configurations of these monosaccharides.

Graphical abstract: Collision-induced dissociation of sodiated glucose, galactose, and mannose, and the identification of anomeric configurations

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Publication details

The article was received on 13 Jun 2018, accepted on 06 Jul 2018 and first published on 07 Jul 2018


Article type: Paper
DOI: 10.1039/C8CP03753A
Citation: Phys. Chem. Chem. Phys., 2018,20, 19614-19624
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    Collision-induced dissociation of sodiated glucose, galactose, and mannose, and the identification of anomeric configurations

    H. T. Huynh, H. T. Phan, P. Hsu, J. Chen, H. S. Nguan, S. Tsai, T. Roongcharoen, C. Y. Liew, C. Ni and J. Kuo, Phys. Chem. Chem. Phys., 2018, 20, 19614
    DOI: 10.1039/C8CP03753A

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