title: Conformational differences between O- and C-glycosides: the alpha-O-man-(1-->1)-beta-Gal/alpha-C-Man-(1-->1)-beta-Gal case--a decisive demonstration of the importance of the exo-anomeric effect on the conformation of glycosides.
abstract: The conformational behavior of alpha-O-Man-(1-->1)-beta-Gal (1) and its C-analogue (2) has been studied using J/NOE NMR data, molecular mechanics, molecular dynamics, and ab initio calculations. The population distribution around the glycosidic linkages of 1 and 2 is rather different, especially for the alpha-Man linkage. A lower limit for the exo-anomeric effect in water has been experimentally determined.
authors.affiliation: Departamento de Química Orgánica Biológica, CSIC, Madrid, Spain.
authors.forename: J L
authors.initials: JL
authors.lastname: Asensio
authors.forename: F J
authors.initials: FJ
authors.lastname: Cañada
authors.forename: X
authors.initials: X
authors.lastname: Cheng
authors.forename: N
authors.initials: N
authors.lastname: Khan
authors.forename: D R
authors.initials: DR
authors.lastname: Mootoo
authors.forename: J
authors.initials: J
authors.lastname: Jiménez-Barbero
mesh_terms: D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000737:chemistry; D005690:Galactose / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000737:chemistry; D008958:Models, Molecular
chemical_list: D004187:Disaccharides; D006027:Glycosides; D008358:Mannose; D005690:Galactose