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Alpha-O-linked glycopeptide mimetics: synthesis, conformation analysis, and interactions with viscumin, a galactoside-binding model lectin

AuthorsJiménez-Barbero, Jesús ; Dragoni, Elisa; Venturi, Chiara; Nannucci, Federico; Ardá, Ana ; Fontanella, Marco ; André, Sabine; Cañada, F. Javier ; Gabius, Hans-Joachim; Nativi, Cristina
drug design
molecular modeling
NMR electroscopy
Issue Date12-Oct-2009
CitationChemistry - A European Journal 15:10423-31(2009)
AbstractEfficient cycloaddition of a silylidene-protected galactal with a suitable heterodiene yielded the basis for a facile diastereoselective route to a glycopeptide-mimetic scaffold. Its carbohydrate part was further extended by beta1-3-linked galactosylation. The pyranose rings retain their (4)C(1) chair conformation, as shown by molecular modeling and NMR spectroscopy, and the typical exo-anomeric geometry was observed for the disaccharide. The expected bioactivity was ascertained by saturation-transfer-difference NMR spectroscopy by using the galactoside-specific plant toxin viscumin as a model lectin. The experimental part was complemented by molecular docking. The described synthetic route and the strategic combination of computational and experimental techniques to reveal conformational properties and bioactivity establish the prepared alpha-O-linked glycopeptide mimetics as promising candidates for further exploitation of this scaffold to give O-glycans for lectin blocking and vaccination
Description9 páginas, 8 figuras, 2 tablas, 5 esquemas -- PAGS nros. 10423-10431
Publisher version (URL)http:dx.doi.org/10.1002/chem.200901077
Appears in Collections:(CIB) Artículos
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