Unusual conformational behavior of trisaccharides containing N-acetylglucosamine.
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.
Liao
Liang
L
Department of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1.
Robertson
Valerie
V
Auzanneau
France-Isabelle
FI
D000117:Acetylglucosamine / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002247:Carbon Isotopes; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008958:Models, Molecular; D008969:Molecular Sequence Data; D011522:Protons; D012015:Reference Standards; D014312:Trisaccharides / Q000737:chemistry*
D002247:Carbon Isotopes; D011522:Protons; D014312:Trisaccharides; D000117:Acetylglucosamine