Synthesis and Characterization of High Molecular Weight Polyacrylamide Nanoparticles by Inverse-emulsion Polymerization

The synthesis of vinylic derivatives of 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose1a as polymerizable glycomonomer moieties was accomplished. Firstly,in order to carry out the selective reactions on polyhydroxylic carbohydratemolecules, all of the hydroxyl groups of D-mannopyranose 1 except one of thehydroxyl groups in anomeric centre (C1-OH) were protected with the formation of acetalcompound. Then the acetal protected derivative 1a was reacted with acryloyl chloride,methacryloyl chloride, methacrylic anhydride and ρ-(chloromethyl)styrene in thepresence of triethylamine and sodium hydride to give the vinyl saccharide monomericcompounds 2a, 2b and 2c. Then monomers 1-O-acryloyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside 2a, 1-O-methacryloyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside2b and ρ-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranose-1-oxymethyl)styrene 2c were isolated with column chromatography method using a gradient ofhexane and ethyl acetate as eluant. The homopolymerization of above mentionedsugar-protected glycomonomers led to poly(1-O-acryloyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside) P3a, poly(1-O-methacryloyl-2,3:5,6-di-O-iso-propylidene-α-Dmannofuranoside)P3b and poly[ρ-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranose-1-oxymethyl)styrene] P3c in the presence of benzoyl peroxide by heating at 60°C usingsolvent. The obtained glycopolymers were purified through solvent and non-solventsystems. The structure of all purified glycomonomers and glycopolymers wereconfirmed using 1H, 13C and 2D NMR and FTIR. The molecular weights of the obtainedglycopolymers were determined using gel permeation chromatography (GPC).