Rapid synthesis of self-assembling 1,2-thiomannobioside glycoconjugates as potential multivalent ligands of mannose-binding lectins

Among the pathogen-associated carbohydrate patterns, the Man(α1→2)Man α disaccharide motif is of particular interest because its multivalent derivatives are considered as potential antiviral or antibacterial agents through interaction with mannose-binding lectins. We present a straightforward synthesis of amphiphilic compounds containing a hydrolytically stable S-linked 1,2-mannobioside residue, a tetraethylene glycol linker to ensure water solubility and various lipophilic carriers such as a hexadecyl chain and two pyrrolidinofullerene derivatives. According to a dynamic light scattering study, the obtained amphiphiles form nanoscale aggregates in water producing multivalent presentation of the thiomannobioside residue.