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Updated: Aug 13, 2026

Metabolic Glycoengineering of Sialic Acid Using N-acyl-modified Mannosamines
Published on: November 25, 2017
Glycosylation of N-acetylglucosamine: imidate formation and unexpected conformation
Liang Liao1, France-Isabelle Auzanneau
1Department of Chemistry and Biochemistry, University of Guelph, Guelph, Ontario N1G 2W1, Canada.
Abstract:
[structure: see text] Rhamnosylation in mild conditions of a disaccharide containing N-acetylglucosamine afforded the imidate 6 while at higher temperature and concentration of promoter trisaccharide 7 was isolated. The kinetic imidate 6 was independently rearranged in 50% yield to the thermodynamic trisaccharide 7. Comparative NMR studies of 7 in CDCl(3) and DMSO-d(6) suggest the formation of a nonchair conformation in CDCl(3). The structure of 7 was confirmed through the independent synthesis of the N-acetylacetamido trisaccharide 11.
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