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Updated: Aug 15, 2026

Metabolic Glycoengineering of Sialic Acid Using N-acyl-modified Mannosamines
Published on: November 25, 2017
Unusual conformational behavior of trisaccharides containing N-acetylglucosamine
Liang Liao1, Valerie Robertson, France-Isabelle Auzanneau
1Department of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1.
Abstract:
Protected trisaccharides containing N-acetylglucosamine can adopt unexpected conformations through the formation of hydrogen bonds involving the amide group. This conformational behavior was observed by NMR spectroscopy when three protected trisaccharides were dissolved in deuterated chloroform and to a lesser extent in deuterated dichloromethane. In contrast, NMR spectra of the same analogues acquired in the hydrogen bond-accepting solvents deuterated acetonitrile and dimethylsulfoxide showed that the N-acetylglucosamine residues adopted the expected 4C1 conformation.
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