Synthesis and structural investigation of a series of mannose-containing oligosaccharides using mass spectrometry

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.

Pendrill, RobertStockholms universitet,Institutionen för organisk kemi (författare)
Kanie, Y. (författare)
Ito, Y. (författare)
Widmalm, GöranStockholms universitet,Institutionen för organisk kemi(Swepub:su)gw (författare)
Kanie, O. (författare)
Stockholms universitetInstitutionen för organisk kemi (creator_code:org_t)

Ingår i:Organic and biomolecular chemistry: Royal Society of Chemistry (RSC)16:2, s. 228-2381477-05201477-0539

Av författaren/redakt...: Daikoku, S.; Pendrill, Robert; Kanie, Y.; Ito, Y.; Widmalm, Göran; Kanie, O.

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