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

Authors
Asensio, JL Canada, FJ Chen, XH Khan, N Mootoo, DR Jimenez-Barbero, J
Citation
Jl. Asensio et al., 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, CHEM-EUR J, 6(6), 2000, pp. 1035-1041
Citations number
29
Categorie Soggetti
Chemistry
Journal title
CHEMISTRY-A EUROPEAN JOURNAL
ISSN journal
09476539 → ACNP
Volume
6
Issue
6
Year of publication
2000
Pages
1035 - 1041
Database
ISI
SICI code
0947-6539(20000317)6:6<1035:CDBOAC>2.0.ZU;2-Z
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, m olecular dynamics, and ab initio calculations. The population distribution around the glycosidic linkages of 1 and 2 is rather different, especially f or the alpha-Man linkage. A lower limit for the exo-anomeric effect in wate r has been experimentally determined.