Multivalent interactions between carbohydrates and proteins enable a broad range of selective interactions of critical biological importance. However, in vitro control over the placement of multiple carbohydrate groups at nanometer length scales to enable controlled multivalent interactions is a significant challenge. Therefore, developing a modular, biocompatible scaffold with precisely controlled glycan density and orientation could lead to improved glycan screening array performance by more closely replicating multivalent binding geometries observed in vivo. Here, we show that diyne amphiphiles with carbohydrate headgroups can be assembled on highly oriented pyrolytic graphite (HOPG) to generate nm-resolution carbohydrate patterns, which are then photopolymerized and covalently transferred to the surfaces of acrylamide hydrogels. Despite the significant heterogeneity in the hydrogel substrate, transferred patterns of appropriate carbohydrates N-acetyl-D-glucosamine (GlcNAc) enable highly selective multivalent interactions with wheat germ agglutinin (WGA), a model lectin that exhibits multivalent binding with appropriately spaced GlcNAc moieties. Additionally, WGA binding selectivity can be modulated by the choice of alkyl chain structure, suggesting that this can be used to further control carbohydrate presentation at the interface. More broadly, this approach may have potential utility in the generation of glycan arrays, and in designing interfaces for controlled interactions with cells.

Precision nanostructured presentation of glycans at interfaces for multivalent binding

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ACS Fall 2022

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