Interference with oligosaccharide-mediated recognition events can be achieved using functional mimics of carbohydrates, that could thus be used to modulate / alter signal transmission, or to prevent the onset of diseases. In recent years our laboratory has designed and prepared glycomimetic inhibitors of well-known target lectins (cholera toxin, DC-SIGN) using conformationally stable cyclohexane diols to replace structural units of galactose or mannose in the context of oligosaccharide sequences.1,2 More recently, we have concentrated our attention on -glycosyl amides as mimics of -glycosides potentially endowed with metabolical stability properties.3,4 The presentation will discuss the synthetic methodology developed to synthesize -glycosyl amides5 and to incorporate them in (unnatural) glycopeptides sequences, as well as some of the applications we are exploring for this type of carbohydrate mimics.
Recent advances in oligosaccharide mimics / A. Bernardi. ((Intervento presentato al 16. convegno Eurocarb : European carbohydrate symposium tenutosi a Sorrento nel 2011.
Recent advances in oligosaccharide mimics
A. BernardiPrimo
2011
Abstract
Interference with oligosaccharide-mediated recognition events can be achieved using functional mimics of carbohydrates, that could thus be used to modulate / alter signal transmission, or to prevent the onset of diseases. In recent years our laboratory has designed and prepared glycomimetic inhibitors of well-known target lectins (cholera toxin, DC-SIGN) using conformationally stable cyclohexane diols to replace structural units of galactose or mannose in the context of oligosaccharide sequences.1,2 More recently, we have concentrated our attention on -glycosyl amides as mimics of -glycosides potentially endowed with metabolical stability properties.3,4 The presentation will discuss the synthetic methodology developed to synthesize -glycosyl amides5 and to incorporate them in (unnatural) glycopeptides sequences, as well as some of the applications we are exploring for this type of carbohydrate mimics.Pubblicazioni consigliate
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