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      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.

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          Author and article information

          Journal
          ChemMedChem
          ChemMedChem
          Wiley
          1860-7187
          1860-7179
          Jan 22 2018
          : 13
          : 2
          Affiliations
          [1 ] Galecto Biotech AB, Sahlgrenska Science Park, Medicinaregatan 8A, 413 46, Gothenburg, Sweden.
          [2 ] Centre for Analysis and Synthesis, Department of Chemistry, Lund University, Box 124, 221 00, Lund, Sweden.
          [3 ] Red Glead Discovery AB, Medicon Village, 223 63, Lund, Sweden.
          [4 ] SARomics Biostructures AB, Medicon Village, 223 63, Lund, Sweden.
          [5 ] Biochemistry and Structural Biology, Center for Molecular Protein Science, Department of Chemistry, Lund University, Box 124, 221 00, Lund, Sweden.
          [6 ] Department of Laboratory Medicine, Section MIG, Lund University BMC-C1228b, Klinikgatan 28, 221 84, Lund, Sweden.
          Article
          10.1002/cmdc.201700744
          29194992

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