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The role of the mobile proton in fucose migration

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Lettow,  Maike
Molecular Physics, Fritz Haber Institute, Max Planck Society;
Institute of Chemistry and Biochemistry, Freie Universität Berlin;

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Mucha,  Eike
Molecular Physics, Fritz Haber Institute, Max Planck Society;
Institute of Chemistry and Biochemistry, Freie Universität Berlin;

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Manz,  Christian
Molecular Physics, Fritz Haber Institute, Max Planck Society;
Institute of Chemistry and Biochemistry, Freie Universität Berlin;

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Thomas,  Daniel
Molecular Physics, Fritz Haber Institute, Max Planck Society;

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Marianski,  Mateusz
Molecular Physics, Fritz Haber Institute, Max Planck Society;
Hunter CollegeThe City University of New York;

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Meijer,  Gerard
Molecular Physics, Fritz Haber Institute, Max Planck Society;

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Helden,  Gert von
Molecular Physics, Fritz Haber Institute, Max Planck Society;

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Pagel,  Kevin
Molecular Physics, Fritz Haber Institute, Max Planck Society;
Institute of Chemistry and Biochemistry, Freie Universität Berlin;

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Citation

Lettow, M., Mucha, E., Manz, C., Thomas, D., Marianski, M., Meijer, G., et al. (2019). The role of the mobile proton in fucose migration. Analytical and Bioanalytical Chemistry, 411(19), 4637-4645. doi:10.1007/s00216-019-01657-w.


Cite as: http://hdl.handle.net/21.11116/0000-0003-1D86-6
Abstract
Fucose migration reactions represent a substantial challenge in the analysis of fucosylated glycan structures by mass spectrometry. In addition to the well-established observation of transposed fucose residues in glycan-dissociation product ions, recent experiments show that the rearrangement can also occur in intact glycan ions. These results suggest a low-energy barrier for migration of the fucose residue and broaden the relevance of fucose migration to include other types of mass spectrometry experiments, including ion mobility-mass spectrometry and ion spectroscopy. In this work, we utilize cold-ion infrared spectroscopy to provide further insight into glycan scrambling in intact glycan ions. Our results show that the mobility of the proton is a prerequisite for the migration reaction. For the prototypical fucosylated glycans Lewis x and blood group antigen H-2, the formation of adduct ions or the addition of functional groups with variable proton affinity yields significant differences in the infrared spectra. These changes correlate well with the promotion or inhibition of fucose migration through the presence or absence of a mobile proton.