Abstract
Oligosaccharides 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.
Highlights
Broad variety of cell–cell interactions related to invading bacteria, viruses and cancer cells [1,2,3,4] and to play central roles in post-translational modifications of proteins [5,6,7], cell–cell communication [8] and immune response to pathogens [7,9,10,11]
Taking into account the increasing importance of glycobiology and the difficulties associated to the synthesis of carbohydratebased libraries, several approaches based on the assembly of sugar building blocks through amide and pseudoamide linkages have been developed by different research groups over the last few years
The results showed that the binding of a 21-mer ribonucleic guanidine (RNG)/DNA chimera containing six guanidinium linkages is more than 104-fold stronger than the binding of its 21-mer DNA counterpart
Summary
Address: 1Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Prof.
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