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Unique cleavage of 2-acetamido-2-deoxy-d-glucose from the reducing end of biantennary complex type oligosaccharides
Authors:Takefumi Murase
Affiliation:a International Graduate School of Arts and Sciences, Yokohama City University, 22-2, Seto, Kanazawa-ku, Yokohama 236-0027, Japan
b Department of Chemistry, Faculty of Science, Osaka University, 1-1, Machikaneyama, Toyonaka 560-0043, Japan
Abstract:Basic treatment of a biantennary complex-type sialyloligosaccharide, as well as its asialo form, was found to lead to the specific cleavage of 2-acetamido-2-deoxy-d-glucose (GlcNAc) from the reducing end. The resultant oligosaccharides were identical to those prepared by treatment with endo-β-glycosidase-M, which cleaves the glycosidic bond between two GlcNAc residues at the reducing end of N-linked oligosaccharides. In addition, mechanistic studies suggested that an elimination reaction in the reducing-end terminal GlcNAc residue causes this specific cleavage reaction.
Keywords:Oligosaccharide   Decomposition reaction   Peeling reaction   Glycosyl donor
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