Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 30, Pages 5916-5923Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob07135e
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Funding
- FCT-Portugal [SFRH/BPD/65462/2009]
- Universita' degli Studi di Milano (PUR)
- Ministero dell'Istruzione Universita' e Ricerca [2008J4YNJY]
- MICINN [CTQ2009-08536]
- EC GlycoHIT project [260600]
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Natural N-glycosylation involves a beta-anomeric linkage connecting the sugar to one asparagine residue of the protein. We herein report NMR- and modelling-based data on glycomimetics containing alpha-glycosidic linkages. The bioactivity of alpha-Gal-containing glycopeptides has been documented by revealing binding to two plant lectins, i.e. a potent beta-trefoil toxin (Viscum album agglutinin) and beta-sandwich lectin (Erythrina corallodendron agglutinin), by NMR protocols. Docking provided insights into the 3D structures of the resulting complexes. These results provide the basis to introduce alpha-substituted neoglycopeptides to the toolbox of scaffold for the design of potent lectin inhibitors.
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