Premium
Conformational Behavior of C ‐Glycosyl Analogues of Sialyl‐α‐(2→3)‐Galactose
Author(s) -
Poveda Ana,
Asensio Juan Luis,
Polat Tülay,
Bazin Hélèn,
Linhardt Robert J.,
JiménezBarbero Jesús
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200005)2000:9<1805::aid-ejoc1805>3.0.co;2-a
Subject(s) - chemistry , glycosyl , galactose , stereochemistry , organic chemistry
The conformational behavior of the C ‐glycosyl analogue of sialyl‐α‐(2→3)‐galactose, synthesized as a glycosidase inhibitor, has been studied using a combination of NMR spectroscopy ( J and NOE data) and molecular dynamics calculations. The obtained results show that the population distribution of conformers with respect to the orientation about the pseudo‐glycosidic linkages is mainly controlled by steric interactions. This is in contrast to findings made for O ‐glycosides. In these natural compounds, the conformational behavior about the glycosidic linkage Φ is mainly governed by the exo ‐anomeric effect.