Biopolymers such as polynucleic acids and proteins have been widely investigated in order to correlate sequence and structure to function. Polysaccharides (the third class of biopolymers) have historically been recognized as structural materials and as an energy source, and can also play important roles in biological processes such as pathogen recognition, viral entry and immune function, and cell adhesion and signal transduction. However, the lack of tools for the rapid synthesis and characterization of well-defined oligo- and polysaccharides has hampered the investigation of their complex roles in biology, and limited their exploitation for biomedical applications. Synthetic (laboratory) techniques for glycopolymers generally fall into one of two approaches. Well-defined oligo- and polysaccharides can be synthesized via a tedious protection-deprotection sequence, but generally only small amounts of product are obtained. Alternatively, monomers containing a saccharide group are polymerized. Products are high molecular weight, typically linear and only contain one or two residues, and lack specificity in biological interactions beyond the cluster glycoside effect. More efficient synthetic techniques are therefore needed to produce both short and long chain glycomimetics with well-defined biomimetic structures to achieve increased bioactivity. We report a series of glycoacrylates, glycoinitiators and glycoinimers, and optimized their polymerization. We demonstrate that branched polymers incorporating the mannose unit into the branching repeat unit show a higher affinity for mannose binding lectin (MBL) than linear polymers of the same molecular weight. Furthermore, incorporation of the glycoside in the branching repeat unit enhances the polymer's interaction with MBL, and this affinity increases with increasing branching density. In addition to producing linear and branched glycomimetics, we are also polymerizing the glycomonomers and glycoinimers from protein-based initiators to obtain protein-glycomimetic conjugates in which the glycol-component is linear or branched. We have also incorporated glycoacrylate monomers into PEG-based scaffolds and investigate their interaction with cells.

Synthesis, characterization and bioactivity of glycomimetic polymers

247th National Meeting (2014)

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