English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/53289
Share/Impact:
Statistics
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:
DC FieldValueLanguage
dc.contributor.authorJiménez-Barbero, Jesús-
dc.contributor.authorDragoni, Elisa-
dc.contributor.authorVenturi, Chiara-
dc.contributor.authorNannucci, Federico-
dc.contributor.authorArdá, Ana-
dc.contributor.authorFontanella, Marco-
dc.contributor.authorAndré, Sabine-
dc.contributor.authorCañada, F. Javier-
dc.contributor.authorGabius, Hans-Joachim-
dc.contributor.authorNativi, Cristina-
dc.date.accessioned2012-07-13T10:00:47Z-
dc.date.available2012-07-13T10:00:47Z-
dc.date.issued2009-10-12-
dc.identifier.citationChemistry - A European Journal 15:10423-31(2009)es_ES
dc.identifier.issn0947-6539-
dc.identifier.urihttp://hdl.handle.net/10261/53289-
dc.description9 páginas, 8 figuras, 2 tablas, 5 esquemas -- PAGS nros. 10423-10431es_ES
dc.description.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 vaccinationes_ES
dc.description.sponsorshipThis work was supported by a grant from the MinistryofScience and Innovation of Spain (CTQ2006-10874-C02-01/BQU) and by an EC Marie Curie Research Training Network grant (MCRTN-CT-2005-19561). The authors thank the Ente Cassa di Risparmio di Firenze for a PhD grant to E.D.es_ES
dc.language.isoenges_ES
dc.publisherWiley-VCHes_ES
dc.rightsclosedAccesses_ES
dc.subjectcarbohydrateses_ES
dc.subjectdrug designes_ES
dc.subjectglycoproteinses_ES
dc.subjectlectinses_ES
dc.subjectmolecular modelinges_ES
dc.subjectNMR electroscopyes_ES
dc.titleAlpha-O-linked glycopeptide mimetics: synthesis, conformation analysis, and interactions with viscumin, a galactoside-binding model lectines_ES
dc.typeArtículoes_ES
dc.identifier.doi10.1002/chem.200901077-
dc.description.peerreviewedPeer reviewedes_ES
dc.relation.publisherversionhttp:dx.doi.org/10.1002/chem.200901077es_ES
dc.identifier.e-issn1521-3765-
Appears in Collections:(CIB) Artículos
Files in This Item:
File Description SizeFormat 
restringido.pdf21,67 kBAdobe PDFThumbnail
View/Open
Show simple item record
 

Related articles:


WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.