Conformational Behavoir of C-Glycosyl Analogues of Sialyl a-(2,3) Galactose

Poveda, A.
Asensio, J.L.
Polat, T.
Bazin, H.
Linhardt, Robert J.
Jiminez-Barbero, J.
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Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
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Conformational Behavoir of C-Glycosyl Analogues of Sialyl a-(2,3) Galactose, A. Poveda, J.L. Asensio, T. Polat, H. Bazin, R. J. Linhardt, J. Jiminez-Barbero, European Journal of Organic Chemistry, 1805-1813, 2000.
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.
European Journal of Organic Chemistry, 1805-1813
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