Serine versus Threonine Glycosylation: The Methyl Group Causes a Drastic Alteration on the Carbohydrate Orientation and on the Surrounding Water Shell
- Corzana, F. 2
- Busto, J.H. 2
- Jiménez-Osés, G. 2
- De Luis, M.G. 2
- Asensio, J.L. 3
- Jiménez-Barbero, J. 1
- Peregrina, J.M. 2
- Avenoza, A. 2
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1
Centro de Investigaciones Biológicas
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2
Universidad de La Rioja
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3
Instituto de Química Orgánica General
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ISSN: 0002-7863
Argitalpen urtea: 2007
Alea: 129
Zenbakia: 30
Orrialdeak: 9458-9467
Mota: Artikulua
Beste argitalpen batzuk: Journal of the American Chemical Society
Lotura duten proiektuak
Laburpena
Different behavior has been observed for the ψ torsion angle of the glycosidic linkages of D-GalNAc-Ser and D-GalNAc-Thr motifs, allowing the carbohydrate moiety to adopt a completely different orientation. In addition, the fact that the water pockets found in α-D-GalNAc-Thr differ from those obtained for its serine analogue could be related to the different capability that the two model glycopeptides have to structure the surrounding water. This fact could have important biological inferences (i.e., antifreeze activity). © 2007 American Chemical Society.