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- W3158864496 abstract "Abstract Galectins are a galactoside specific subclass of carbohydrate binding proteins (lectins) involved in various cellular activities, certain cancers, infections, inflammations, and many other biological processes. The molecular basis for the selectivity of galectins is well‐documented and revolves around appropriate interaction complementarity: an aromatic residue for C−H⋅⋅⋅π interactions and polar residues for (charge assisted) hydrogen bonds with the axial hydroxyl group of a galactoside. However, no synthetic mimics are currently available. We now report on the design and synthesis of the first galectin mimic ( 6 ), and show that it has a higher than 65‐fold preference for n ‐octyl‐β‐galactoside ( 8 ) over n ‐octyl‐β‐glucoside ( 7 ) in CD 2 Cl 2 containing 5 % [D 6 ]DMSO (with K a ≥4500 M −1 for 6 : 8 ). Molecular modeling informed by nOe studies reveal a high degree of interaction complementarity between 6 and galactoside 8 , which is very similar to the interaction complementarity found in natural galectins." @default.
- W3158864496 created "2021-05-10" @default.
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- W3158864496 date "2021-06-15" @default.
- W3158864496 modified "2023-10-16" @default.
- W3158864496 title "A Synthetic Galectin Mimic" @default.
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- W3158864496 doi "https://doi.org/10.1002/anie.202104924" @default.
- W3158864496 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/8361779" @default.
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