English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/37544
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:
Title

Urea-, Thiourea-, and Guanidine-Linked Glycooligomers as Phosphate Binders in Water

AuthorsJiménez Blanco, José L.; Bootello, Purificación; Benito, Juan M. ; Ortiz-Mellet, Carmen; García-Fernández, José Manuel
KeywordsCarbohydrates
Guanidine
Oligosaccharides
Phosphates
Stereoisomerism
Thiourea
Urea
Water
Molecular sequence data
Issue Date13-Jun-2006
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 71(14): 5136-5143 (2006)
AbstractBeta-(1-->6)-linked pseudodi- and pseudotrisaccharides incorporating alternating pseudoamide-type (urea, thiourea, guanidine) intersaccharide bridges have been prepared and evaluated as phosphate binders in water. The monosaccharide subunits induce the Z,Z rotameric form at the pseudoamide segments, thus favoring their participation in bidentate hydrogen-bond interactions with oxoanions. Moreover, the conformational properties about the anomeric C-1-N bonds and the sugar C-5--C-6 bonds privilege orientations that facilitate both the desolvation of the incoming anionic guest and the stabilization of the complex by cooperative interactions. Measurable association constants (K(as)) toward dimethyl and, especially, phenyl phosphate were obtained from NMR titration experiments for both series of glucooligomers, the binding affinity being strongly dependent on the nature of the pseudoamide functionality. Guanidinium derivatives, for which charge neutralization was expected to contribute to phosphate binding, were superior to the neutral thiourea and urea derivatives (K(as) = 48-60 M(-1) for 1:1 complexes with phenyl phosphate dianion). Interestingly, the thiourea oligomers exhibited association constants of the same order of magnitude (K(as) = 25-40 M(-1)), much higher than those observed for the urea analogues (K(as) = 2-3 M(-1)), which is ascribed to a less efficient solvation of the thiocarbonyl derivatives.
Description8 páginas, 5 figuras, 1 tabla, esquemas.
Publisher version (URL)http://dx.doi.org/10.1021/jo060360q
URIhttp://hdl.handle.net/10261/37544
DOI10.1021/jo060360q
ISSN0022-3263
Appears in Collections:(IIQ) Artículos
Files in This Item:
There are no files associated with this item.
Show full item record
Review this work
 

Related articles:


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