Synthesis of a polyurea from a glucose- or mannose-containing N-alkyl urea peptoid oligomer.

ABSTRACT 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. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 5230-5238 [ABSTRACT FROM AUTHOR]