Evaluation of steric effects on the exocyclic conformations of 6-C-methyl-substituted 2-acetamido-2-deoxy-beta-D-glucopyranosides.
Introduction of a stereodefined methyl group at the C-6 position of N-acetylglucosamine mono- and disaccharides creates a strong and predictable orientational bias on the geminal C-6 hydroxyl in solution, as determined by (1)H-(1)H and (13)C-(1)H NMR coupling constants. The conformational directing effect is more pronounced in the disaccharides because of the greater steric demand imposed by the neighboring glycosidic unit.
Achkar
Jihane
J
Department of Chemistry, Purdue University, 1393 Brown Building, West Lafayette, IN 47907-1393, USA.
Sanchez-Larraza
Isabel
I
Wei
Alexander
A
D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000737:chemistry*; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods
D004187:Disaccharides; D006027:Glycosides; C075822:glucopyranosylamine; D005944:Glucosamine