Synthesis of a polyurea from a glucose- or mannose-containingN-alkyl urea peptoid oligomer

N-alkyl urea peptoid oligomers containing glucose or mannose have been synthesized and characterized. The oligomers were subsequently polymerized using a step-growth polymerization with hexamethylene diisocyanate. Equal moles of both monomers were used to guarantee high-molecular weight polymers. The polymers were characterized by gel permeation chromatography, nuclear magnetic resonance, and Fourier-transform infrared spectroscopy, and contact angle measurements of solvent cast thin films. Sulfation of the final polymers was achieved using a SO3/pyridine complex in pyridine to afford the heparin biomimetics. The average degree of sulfation was calculated to be 3.5 sulfates per saccharide as measured by elemental analysis.