Interactions of Glycopolymers with Assemblies of Peptide Amphiphiles via Dynamic Covalent Bonding

In this work, peptide amphiphile (PA) with benzoboroxole (BOB) group at the hydrophilic end was prepared and assembled into fibers (PAA) with BOB group on the fiber surface. Then glycopolymer with mannopyranoside as pendent group interacted with the PAA via dynamic covalent bond between sugar and BOB. By combining the results from 2D 1H NMR spectroscopy, the exact binding mode of mannopyranoside pendent group and BOB, i.e., mannopyranoside participated by its diol on 2,3-position instead of that on 4,6-position, which was clearly observed on the fiber surface. The success in determining this binding mode in macroscopic material was due to the high density of BOB on PAA and the multivalent effect between the multiple BOB moieties on fiber surface and repeating mannopyranoside groups of the glycopolymer.