Synthesis and Determination of Polymerization Rate Constants of Glucose-Based Monomers

To prepare non-ionic amphiphilic polymers usable for solubilizing integral membrane proteins, hydrophilic and amphiphilic beta-D-glucose-based tris(hydroxymethyl) acrylamidomethane monomers were synthesized and their radical homopolymerization rate constants (fk(p)(2)/k(t)) were determined. The polymerization kinetics, monitored by H-1-NMR, were carried out in THF in the presence of AIBN as radical initiator. The plot of monomer conversion as a function of time followed Tobolsky's equation. The number of hydroxyl groups, as well as the nature of the substituents grafted onto the hydroxyl groups, was found to alter the rates of polymerization. While the steric hindrance significantly affected the kinetics, intermolecular hydrogen bonds between hydroxyl groups, as demonstrated by NMR investigations at different concentrations and temperatures, may also play a role in the rate constants of polymerization. (C) Koninklijke Brill NV, Leiden, 2011