Molecular recognition of carbohydrates plays vital roles in biology but has been difficult to achieve with synthetic receptors. Covalent imprinting of carbohydrates in boroxole-functionalized cross-linked micelles yields polymeric nanoparticle receptors for a wide variety of mono- and oligosaccharides. The protein-sized “synthetic lectins” bind glucose, mannose, and galactose with &gt;100:1 selectivity and distinguish oligosaccharides based on their monosaccharide building blocks, glycosidic linkages, chain length. They can be generated directly from cleaved glycans from glycoproteins and used to extract targeted glycoproteins from mixtures. They display competitive affinities for their targeted glycans in comparison to natural lectins and can suppress enzymatic hydrolysis of targeted glycans.<br/><br/>When installed with acidic functionalities, the molecularly imprinted synthetic lectins turn into artificial glycosidases that hydrolyze glycans with predetermined selectivity. Separation of products can be accomplished through in-situ dialysis and the catalysts left behind could be reused multiple times. As an example of application, synthetic mimics of endocellulase, exocellulase, and β-glucosidase were prepared for synergistic hydrolysis of cellulose—a key step in biomass conversion. The activity of the synthetic blend at 90 °C in pH 6.5 buffer more than doubled that of <i>Aspergillus niger</i> cellulase at pH 5 and 37 °C and reached 44% of that of a commercial cellulase blend from Novozyme. As robust cross-linked polymeric nanoparticles, the synthetic catalysts showed little change in activity after preheated at 90 °C for 3 days and maintained 76% of activity after 10 reaction cycles.

Molecularly imprinted nanoparticles as synthetic mimics of lectins and glycosidases

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