Use of chloromethylstyrene as a supporter for convenient preparation of carbohydrate monomer and glycopolymers

A convenient access for glycopolymers was accomplished by using a styrene-modified glycomonomer, which was prepared from chloromethylstyrene as a key starting material and N-acetyl-d-glucosamine (GlcNAc) as a model carbohydrate. One-step conversion of the styrene derivative gave an azidostyrene, which was treated with a propargyl GlcNAc to afford a carbohydrate monomer after deprotection in good yield. The water-soluble GlcNAc monomer was polymerized with or without acrylamide to give the corresponding white powdery glycopolymers, which were evaluated for their interaction against wheat germ agglutinin (WGA) on the basis of fluorescence change of tryptophan in WGA.