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Updated: Jun 22, 2026

Identification and Characterization of Protein Glycosylation using Specific Endo- and Exoglycosidases
Published on: December 26, 2011
Evidence for endocyclic cleavage of conformationally restricted glycopyranosides
Shino Manabe1, Kazuyuki Ishii, Daisuke Hashizume
1RIKEN Advanced Science Institute, Wako, Hirosawa, Saitama 351-0198, Japan. smanabe@riken.jp
Abstract:
2,3-trans-Carbamate- and -carbonate-carrying pyranosides were very easily anomerised from the beta to the alpha direction in the presence of a Lewis acid compared to other pyranosides. This reaction is caused by endocyclic cleavage of the pyranosides. Evidence for endocyclic cleavage of conformationally restricted pyranosides in the chair form was obtained by intra- and intermolecular Friedel-Crafts reactions, chloride addition, and reduction of the generated cation. On the other hand, pyranosides with the distorted conformation were never cleaved in an endocyclic manner.
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