Monosaccharide Derivatives with Low‐Nanomolar Lectin Affinity and High Selectivity Based on Combined Fluorine–Amide, Phenyl–Arginine, Sulfur–π, and Halogen Bond Interactions

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Abstract
The design of small and high‐affinity lectin inhibitors remains a major challenge because the natural ligand binding sites of lectin are often shallow and have polar character. Herein we report that derivatizing galactose with un‐natural structural elements that form multiple non‐natural lectin–ligand interactions (orthogonal multipolar fluorine–amide, phenyl–arginine, sulfur–π, and halogen bond) can provide inhibitors with extraordinary affinity (low nanomolar) for the model lectin, galectin‐3, which is more than five orders of magnitude higher than the parent galactose; moreover, is selective over other galectins.
Funding Information
  • Knut och Alice Wallenbergs Stiftelse (KAW 2013.0022)
  • Vetenskapsrådet (621-2012-2978)

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