Recent advances in oligosaccharide mimics

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.