Ion-Mobility Spectrometry Can Assign Exact Fucosyl Positions in Glycans and Prevent Misinterpretation of Mass-Spectrometry Data After Gas-Phase Rearrangement.
carbohydrates
fucose
ion-mobility spectrometry
mass spectrometry
rearrangement
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
02 12 2019
02 12 2019
Historique:
received:
30
07
2019
revised:
04
09
2019
pubmed:
24
9
2019
medline:
24
9
2020
entrez:
24
9
2019
Statut:
ppublish
Résumé
The fucosylation of glycans leads to diverse structures and is associated with many biological and disease processes. The exact determination of fucoside positions by tandem mass spectrometry (MS/MS) is complicated because rearrangements in the gas phase lead to erroneous structural assignments. Here, we demonstrate that the combined use of ion-mobility MS and well-defined synthetic glycan standards can prevent misinterpretation of MS/MS spectra and incorrect structural assignments of fucosylated glycans. We show that fucosyl residues do not migrate to hydroxyl groups but to acetamido moieties of N-acetylneuraminic acid as well as N-acetylglucosamine residues and nucleophilic sites of an anomeric tag, yielding specific isomeric fragment ions. This mechanistic insight enables the characterization of unique IMS arrival-time distributions of the isomers which can be used to accurately determine fucosyl positions in glycans.
Identifiants
pubmed: 31544998
doi: 10.1002/anie.201909623
doi:
Substances chimiques
Gases
0
Ions
0
Polysaccharides
0
Small Molecule Libraries
0
Fucose
28RYY2IV3F
N-Acetylneuraminic Acid
GZP2782OP0
Acetylglucosamine
V956696549
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
17616-17620Subventions
Organisme : Basque Government
Pays : International
Organisme : EU Commission (Marie Skłodowska-Curie)
ID : 749996
Pays : International
Organisme : Netherlands Organization for Scientific Research (NWO)
ID : TOP-PUNT 718.015.003
Pays : International
Organisme : Netherlands Organization for Scientific Research (NWO)
ID : Innovation Fund Chemistry - LIFT 731.016.402
Pays : International
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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