Novel acetylation‐aided migrating rearrangement of uridine‐diphosphate‐N‐acetylglucosamine in electrospray ionization multistage tandem mass spectrometry
Copyright policy )Novel acetylation‐aided migrating rearrangement of uridine‐diphosphate‐N‐acetylglucosamine in electrospray ionization multistage tandem mass spectrometry
AbstractUridine 5′‐diphospho‐N‐acetylglucosamine (UDP‐GlcNAc) is the final product of hexosamine biosynthetic pathway (HSP) and the donor substrate for the modification of nucleocytoplasmic proteins at serine and threonine residues with N‐acetylglucosamine (GlcNAc) catalyzed by O‐GlcNAc transferase (OGT). Many analogs of UDP‐GlcNAc were designed to interfere with the process of protein O‐glycosylation by blocking OGT. A novel rearrangement reaction was observed in which phosphate‐N‐acetylglucosamine moiety migrated to 3′ terminus of ribose in ESI‐MSn of UDP‐GlcNAc. Results from tandem mass spectrometry, control experiments and calculation showed that the phosphate‐N‐acetylglucosamine migration might undergo a pentacoordinate phosphoric intermediate. Furthermore, the acetylation of glucosamine in UDP‐GlcNAc was essential in the migration process. Copyright © 2005 John Wiley & Sons, Ltd.
- Tsinghua University China (People's Republic of)
Models, Molecular, Spectrometry, Mass, Electrospray Ionization, Uridine Diphosphate N-Acetylglucosamine, Acetylation
Models, Molecular, Spectrometry, Mass, Electrospray Ionization, Uridine Diphosphate N-Acetylglucosamine, Acetylation
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