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Conformational Differences Between O‐ and C‐Glycosides: The α ‐ O ‐Man‐(1→1)‐ β ‐Gal/ α ‐ C ‐Man‐(1→1)‐ β ‐Gal Case‐ A Decisive Demonstration of the Importance of the exo ‐Anomeric Effect on the Conformation of Glycosides
Author(s) -
Asensio Juan L.,
Cañada F. Javier,
Cheng Xuhong,
Khan Noshena,
Mootoo David R.,
JiménezBarbero Jesús
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(20000317)6:6<1035::aid-chem1035>3.0.co;2-g
Subject(s) - anomer , stereochemistry , glycoside , chemistry , anomeric effect
The conformational behavior of α ‐O‐Man‐(1→1)‐ β ‐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 α ‐Man linkage. A lower limit for the exo ‐anomeric effect in water has been experimentally determined.