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  • 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.
    Author: Asensio JL, Cañada FJ, Cheng X, Khan N, Mootoo DR, Jiménez-Barbero J.
    Journal: Chemistry; 2000 Mar 17; 6(6):1035-41. PubMed ID: 10785824.
    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.
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