Serine Versus Threonine Glycosylation: the Methyl Group Causes a Drastic Alteration on the Carbohydrate Orientation and on the Surrounding Water Shell

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2007 Jul 10

PMID 17616194

Citations 45

Authors

Francisco Corzana

Jesus H Busto

Gonzalo Jimenez-Oses

Marisa Garcia de Luis

Juan L Asensio

Jesus Jimenez-Barbero

Jesus M Peregrina

Alberto Avenoza

Affiliations

Soon will be listed here.

Abstract

Different behavior has been observed for the psi 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 alpha-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).

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