Evidence for Long-Range Glycosyl Transfer Reactions in the Gas Phase

Document Type

Article

Publication Title

Journal of the American Society for Mass Spectrometry

Department

Chemistry

ISSN

1044-0305

Volume

13

Issue

4

DOI

10.1016/S1044-0305(02)00343-4

First Page

325

Last Page

337

Publication Date

4-1-2002

Abstract

A long-range glycosyl transfer reaction was observed in the collision-induced dissociation Fourier transform (CID FT) mass spectra of benzylamine-labeled and 9-aminofluorene-labeled lacto-N-fucopentaose I (LNFP I) and lacto-N-difucohexaose I (LNDFH I). The transfer reaction was observed for the protonated molecules but not for the sodiated molecules. The long-range glycosyl transfer reaction involved preferentially one of the two L-fucose units in labeled LNDFH I. CID experiments with labeled LNFP I and labeled LNFP II determined the fucose with the greatest propensity for migration. Further experiments were performed to determine the final destination of the migrating fucose. Molecular modeling supported the experiments and reaction mechanisms are proposed.

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