ABSTRACT

Experimental Methods ........................................................................................... 176 General Methods ............................................................................................... 176

General Procedure for Glycosylation ........................................................... 177 1-Azido-3,6-Dioxaoct-8-yl 2,3,4,6-Tetra-O-Acetyl-β-dGalactopyranoside 2 ...................................................................................... 177 1-Azido-3,6-Dioxaoct-8-yl 2,3,6,2′,3′,4′,6′-Hepta-O-Acetyl-βLactoside 4 ................................................................................................ 178

Acknowledgments .................................................................................................. 178 References .............................................................................................................. 180

Carbohydrate-protein interactions are among the most important biological processes taking place in Nature and are involved in numerous normal and pathological phenomena such as cell-cell communication, viral infection, cancer metastasis, or even fecundation.1 While the interaction of a monovalent saccharide is typically weak, with Kd values in the millimolar range, highly speci¥c and strong avidities are reached when multiple carbohydrate epitopes on the surface of a glycoprotein are not localized randomly but are presented for a multivalent interaction with a lectin in the form of clusters, hence the so-called “cluster effect.”2 Over the past decades, to better understand the function(s) of carbohydrate-lectin interactions or as putative therapeutic alternatives, chemists have developed several approaches for the design of multivalent neoglycoconjugates, such as glycoclusters,3 glycodendrimers,4 glycopolymers,5 or glyconanoparticles.6