Macrocyclic Glycoclusters: From Amphiphiles through Nanoparticles to Glycoviruses

Macrocyclic glycocluster amphiphiles are intended to be a covalent-bundle mimic of clustering glycolipid motifs on the cell membrane. They are irreversibly micellized to give glycocluster nanoparticles (GNPs); their masked hydrophobicity endows them with remarkable saccharide specificities in the interactions with biological saccharide receptors. The GNPs also exhibit unprecedented hydrogen-bond capacities; they are agglutinated with Na(2)HPO(4) and assembled on plasmid DNA in a number-, size-, and shape-controlled manner to give artificial glycoviral particles capable of transfection. Thus, the intrinsic function of viruses, that is, cell invasion followed by gene expression, is also intrinsic to size-regulated (approximately 50 nm) glycoviruses. The growth of glycocluster amphiphiles through nanoparticles to glycoviruses reveals a hierarchical adhesion control of the saccharide clusters.