Oligonucleotide Carbohydrate-Centered Galactosyl Cluster Conjugates Synthesized by Click and Phosphoramidite Chemistries

Abstract

Oligonucleotide glycoconjugates with a mannose or galactose core bearing four galactose residues introduced by phosphoramidite chemistry and copper catalyzed azide alkyne 1,3-dipolar cycloaddition (click chemistry) have been synthesized. A first click reaction allowed the introduction on a solid support of a mannose core on which four pentynyl linkers were introduced using a phosphoramidite derivative. After the elongation of the oligonucleotide, a second click reaction performed either on solid support or in solution allowed the introduction of four galactose azide derivatives. Repeating the phosphoramidite and click chemistries afforded an oligonucleotide glycoconjugate dendrimer bearing 16 galactoses on its periphery.