An α2,3-Linked Sialylglycopolymer as a Multivalent Glycoligand Against Avian and Human Influenza Viruses

Abstract

A glycopolymer bearing α2,3-linked sialyltrisaccharides was synthesized by living radical polymerization using a glycomonomer prepared by a protecting-group-free process, direct azidation of the free sialyllactose, and subsequent azide-alkyne cycloaddition. The prepared glycopolymer with pendant 3´-sialyllactose moieties strongly interacted with both avian and human influenza viruses analyzed by the hemagglutination inhibition assay and the quartz crystal microbalance method.

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 ].…”

“…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 ]. Various other reactions have been used, such as those of maleimide and thiol; isocyanate and amine; isothiocyanate and thiol; epoxide and alcohol; azlactone and amine; and activated esters and amine.…”

“…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.…”

Synthesis and Aggregation Behavior of Temperature- and pH-Responsive Glycopolymers as Sugar-Displaying Conjugates

“…We recently reported on the use of a simple protocol for synthesizing glycopolymers from free saccharides without the need for a protecting group [25][26][27]. The protocol featured a direct anomeric activation reaction using a dehydrating condensing agent (often referred to as the Shoda activation) [28,29] and an azide-alkyne cycloaddition reaction (commonly referred to as click chemistry) [30].…”