D-Fructose, L-Sorbose, D-Tagatose, D-Psicose: Functional Methacrylate-Based Glycopolymers of Ketohexoses Possessing Enhanced Boronic Acid Affinity

The unique binding properties of ketohexoses with boronic acids present new opportunities for functional material design. We investigated the binding of D-fructose, L-sorbose, D-tagatose, and D-psicose with four boronic acids (phenylboronic acid (PBA), 3-acetamidophenylboronic acid (AcPBA), benzoxaborole (BOB), and 6-acetamidobenzoxaborole (AcBOB)) in aqueous environment using isothermal titration calorimetry (ITC), finding that D-psicose exhibits exceptional affinity, compared to other ketohexoses. The ketohexose sugars were efficiently converted into isopropylidene-protected methacrylate monomers for polymer formation. These polymers can be deprotected in an acidic condition to yield the side-chain functionalized glycopolymers, providing a versatile platform for strong boronic acid–carbohydrate interactions for dynamic and advanced material design. • Ketohexose binding with different boronic acids, i.e. phenylboronic acid (PBA), 3-acetamidophenylboronic acid (AcPBA), benzoxaborole (BOB), and 6-acetamidobenzoxaborole (AcBOB), were systematically analyzed using isothermal titration calorimetry (ITC). • Ketohexoses show distinct binding with boronic acids, with D-psicose demonstrating notably higher affinity than D-fructose, L-sorbose, and D-tagatose in aqueous conditions. • Ketohexoses were successfully converted into isopropylidene-protected methacrylate monomers, enabling their incorporation into polymer structures. • The resulting glycopolymers show notable binding to boronic acid.