A Synthetic Galectin Mimic
Angewandte Chemie ; doi:10.1002/ange.202104924
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. Despite this knowledge, no synthetic mimics are currently available. Here, we 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% DMSO‐ d 6 (with K a ≥ 4500 M ‐1 for 6 : 8 ). Molecular modelling 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.
Keywords: carbohydrate recognition / galectin mimic / galactosides / molecular recognition / carbohydrates
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