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(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

AuthorsJiménez Blanco, José L.; Ortega-Caballero, Fernando; Ortiz-Mellet, Carmen; García-Fernández, José Manuel
Spaced sugars
Issue Date22-Feb-2010
PublisherBeilstein-Institut zur Förderung der Chemischen Wissenschaften
CitationBeilstein Journal of Organic Chemistry 6(20): (2010)
AbstractOligosaccharides are currently recognised as having functions that influence the entire spectrum of cell activities. However, a distinct disadvantage of naturally occurring oligosaccharides is their metabolic instability in biological systems. Therefore, much effort has been spent in the past two decades on the development of feasible routes to carbohydrate mimetics which can compete with their O-glycosidic counterparts in cell surface adhesion, inhibit carbohydrate processing enzymes, and interfere in the biosynthesis of specific cell surface carbohydrates. Such oligosaccharide mimetics are potential therapeutic agents against HIV and other infections, against cancer, diabetes and other metabolic diseases. An efficient strategy to access this type of compounds is the replacement of the glycosidic linkage by amide or pseudoamide functions such as thiourea, urea and guanidine. In this review we summarise the advances over the last decade in the synthesis of oligosaccharide mimetics that possess amide and pseudoamide linkages, as well as studies focussing on their supramolecular and recognition properties.
Description18 páginas, 26 figuras, 5 esquemas
Publisher version (URL)http://dx.doi.org/10.3762/bjoc.6.20
Appears in Collections:(IIQ) Artículos
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