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Unusual conformational behavior of trisaccharides containingN-acetylglucosamine

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
340
Issue
18
Identifiers
DOI: 10.1016/j.carres.2005.09.025
Keywords
  • Glcnac Conformations
  • Non-Hydrogen Bonding Solvents
  • Unusual Conformations
  • Glcnac-Containing Intermediates
  • Lewis A Analogues

Abstract

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 4C 1 conformation.

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