Glycosylation of surface via post-polymerization modification and hydrazone conjugation
Leman, Deborah Caroline
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As technologies for surface design and synthetic biomaterials advance, the development of cost-effective and simple methods for polymeric bioconjugated surfaces becomes increasingly important. Carbohydrate conjugation to surfaces has routinely been performed through small molecule attachments to complementary chemistries at the interface. This, however, lacks the advantages of polymeric materials and often requires synthetic modification to the sugar residue which may come at a time cost or loss of biological recognition. Polymer-based materials provide avenues to mimic cell membrane presentation of glycans in order to increase binding affinity. To design surfaces with variable density and ratio of functionalities and the ability to be patterned, a “grafted-to” polymeric activated ester, pentafluorophenyl acrylate (PFPA), was utilized. Post-polymerization modification of the surface-grafted polymer with hydrazine resulted in the ability to conjugate carbohydrates via their reducing end. This attachment chemistry was shown to retain the biorecognition by incubation of 3’-sialyllactose conjugated substrates in the presence of Mycoplasma pneumoniae. The bacteria displayed gliding motility comparable to that observed when exposed to sialic acid containing glycoproteins. This process was optimized to achieve cost-effective and mild conditions as a route to conjugation of a wide variety of carbohydrates.