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Título

The Synthesis and Structure of Linear and Dendritic Thiourea-Linked Glycooligomers

AutorJiménez Blanco, José L.; Bootello, Purificación; Ortiz-Mellet, Carmen; García Fernández, José Manuel CSIC ORCID
Palabras claveCarbohydrates
Conformation analysis
Dendrimers
Glycooligomers
Hydrogen bonding
Fecha de publicación10-nov-2005
EditorWiley-VCH
CitaciónEuropean Journal of Organic Chemistry (1): 183-196 (2006)
ResumenAn efficient strategy to produce unnatural glycooligomers containing thiourea intersaccharide bridges has been developed. The presence of the thiourea groups in these oligomers should promote the association with polyphosphates, including nucleic acids, due to the hydrogen-bonding capabilities of the thioureas. Moreover, glycooligomers built from thiourea groups should form complex secondary and tertiary structures due to the interplay of hydrogen bonding and rotational restriction at the bonds adjacent to thiocarbonyl groups. Herein, the preparation and conformational properties of both linear and dendritic architectures are described. This synthetic method relies on the coupling of peracetylated azidoglycosyl isothiocyanates and fully unprotected amine-functionalised growing oligomers. Deacetylation of the hemiacetylated thiourea adduct and reduction of the azido groups allow entry into a new coupling cycle. The procedure is quite general, should be easily extended to molecular diversity-oriented and solid-phase approaches and will allow the investigation of intermolecular interactions.
Descripción14 páginas, 3 figuras, 6 esquemas.
Versión del editorhttp://dx.doi.org/10.1002/ejoc.200500472
URIhttp://hdl.handle.net/10261/37233
DOI10.1002/ejoc.200500472
ISSN1434-193X
E-ISSN1099-0690
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