Globular carbohydrate macromolecule "Sugar Balls", 2. Synthesis of mono(glycopeptide)-persubstituted dendrimers by polymer reaction with sugar-substitutedα-amino acidN-carboxyanhydrides (glycoNCAs)

Abstract

Sugar-substituted α-amino acid N-carboxyanhydrides (glycoNCAs), i.e., O-(tetra-O-acetyl-β-D-glucopyranosyl)-L-serine NCA (2a) and O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine NCA (2b), were successfully used for the introduction of a mono(glycopeptide) unit into each terminal primary amino group of a dendrimer. Well-defined dendrimer-based artificial glycoconjugates, O-(β-D-glucopyranosyl)-L-serine-persubstituted poly(amido amine) (PAMAM) dendrimer (3a) and O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-serine-persubstituted PAMAM dendrimer (3b), were synthesized by polymer reaction of PAMAM dendrimer with 2a and 2b, respectively, followed by deacetylation with hydrazine monohydrate.