Synthesis of Glycopolymer Gold Nanoparticles Decorated with Oligosaccharides via a Protecting-group-free Process and Their Specific Recognition by Lectins

Abstract

Glycopolymers with various pendant oligosaccharides were synthesized from free saccharides without protection of the saccharide hydroxy and carboxy groups. The strategy involved direct anomeric azidation of the free saccharides, copper-catalyzed azide-alkyne cycloaddition, and reversible addition-fragmentation chain transfer polymerization using the glycomonomers and trithiocarbonate derivative as a chain transfer agent. After reducing the trithiocarbonate terminal group on the polymer backbone, the resulting thiol-terminated glycopolymers were immobilized on gold nanoparticles via Au-S bound formation. The glycopolymer-decorated gold nanoparticles in aqueous suspension were specifically recognized by the corresponding lectin, with no measurable nonspecific binding.

Recent Advances in Polymers Bearing Activated Esters for the Synthesis of Glycopolymers by Postpolymerization Modification

“…Huisgen cycloaddition has been employed to synthesize numerous glycomonomers and glycopolymers with the Haddleton, Gibson, Becer, and Miura groups, and many others [ 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 ]. The authors reported the synthesis of glycopolymers by Huisgen cycloaddition in the postpolymerization modification using glycosyl azides, which were directly synthesized from unprotected saccharides using a water-soluble dehydration condensation agent, 2-chloro-1,3-dimethylimidazolinium chloride in water [ 55 , 56 , 57 , 58 , 59 , 60 , 61 ]. Many reports exist on the investigation of the binding affinity of glycopolymers synthesized by Huisgen cycloaddition and other methods used against influenza viruses and their proteins [ 45 , 56 , 57 , 62 , 63 ].…”

“…Click chemistry, such as azide-alkyne cycl (Huisgen cycloaddition) [31][32][33] and thiol-ene reactions [34][35][36][37], is frequently in postpolymerization modification. This is because, in most cases, click chem tions do not produce byproducts, and they enable the facile linking of molecule cycloaddition has been employed to synthesize numerous glycomonomers and ymers with the Haddleton, Gibson, Becer, and Miura groups, and many othe The authors reported the synthesis of glycopolymers by Huisgen cycloaddi postpolymerization modification using glycosyl azides, which were directly s from unprotected saccharides using a water-soluble dehydration condensatio chloro-1,3-dimethylimidazolinium chloride in water [55][56][57][58][59][60][61]. Many reports e investigation of the binding affinity of glycopolymers synthesized by Huisgen tion and other methods used against influenza viruses and their proteins [45,5 Various other reactions have been used, such as those of maleimide and thiol; and amine; isothiocyanate and thiol; epoxide and alcohol; azlactone and amin vated esters and amine.…”