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Synthesis and structural investigation of a series of mannose-containing oligosaccharides using mass spectrometry
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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Number of Authors: 62018 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 16, no 2, p. 228-238Article in journal (Refereed) Published
Abstract [en]

A series of compounds associated with naturally occurring and biologically relevant glycans consisting of alpha-mannosides were prepared and analyzed using collision-induced dissociation (CID), energy-resolved mass spectrometry (ERMS), and H-1 nuclear magnetic resonance spectroscopy. The CID experiments of sodiated species of disaccharides and ERMS experiments revealed that the order of stability of mannosyl linkages was as follows: 6-linked > 4-linked >= 2-linked > 3-linked mannosyl residues. Analysis of linear trisaccharides revealed that the order observed in disaccharides could be applied to higher glycans. A branched trisaccharide showed a distinct dissociation pattern with two constituting disaccharide ions. The estimation of the content of this ion mixture was possible using the disaccharide spectra. The hydrolysis of mannose linkages at 3- and 6-positions in the branched trisaccharide revealed that the 3-linkage was cleaved twice as fast as the 6-linkage. It was observed that the solution-phase hydrolysis and gas-phase dissociation have similar energetics.

Place, publisher, year, edition, pages
2018. Vol. 16, no 2, p. 228-238
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Organic Chemistry
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URN: urn:nbn:se:su:diva-152728DOI: 10.1039/c7ob02723kISI: 000419388500009PubMedID: 29234770OAI: oai:DiVA.org:su-152728DiVA, id: diva2:1182138
Available from: 2018-02-12 Created: 2018-02-12 Last updated: 2018-02-12Bibliographically approved

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Kanie, Y.Ito, Y.Widmalm, GöranKanie, O.
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