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A Synthetic Galectin Mimic.

Brian J J Timmer1, Arjaan Kooijman1, Xander Schaapkens1

  • 1Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH, Amsterdam, The Netherlands.

Angewandte Chemie (International Ed. in English)
|May 8, 2021
PubMed
Summary
This summary is machine-generated.

Researchers designed and synthesized the first synthetic galectin mimic. This novel molecule demonstrates a high preference for galactosides, mimicking natural galectin interactions for potential therapeutic applications.

Keywords:
carbohydrate recognitioncarbohydratesgalactosidesgalectin mimicmolecular recognition

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Area of Science:

  • Carbohydrate Chemistry
  • Chemical Biology
  • Molecular Recognition

Background:

  • Galectins are carbohydrate-binding proteins (lectins) crucial in biological processes like immunity and cancer.
  • Their selectivity relies on specific interactions with galactosides, but synthetic mimics are lacking.

Purpose of the Study:

  • To design and synthesize the first synthetic mimic of galectins.
  • To evaluate its binding selectivity and interaction complementarity compared to natural galectins.

Main Methods:

  • Chemical synthesis of a novel galectin mimic.
  • Binding assays to determine selectivity for n-octyl-β-galactoside over n-octyl-β-glucoside.
  • Molecular modeling and Nuclear Overhauser Effect (nOe) studies to analyze binding interactions.

Main Results:

  • The synthesized compound (6) exhibits a >65-fold preference for n-octyl-β-galactoside (8) over n-octyl-β-glucoside (7).
  • Binding affinity (Ka) for the mimic and galactoside was determined to be ≥4500 M-1.
  • Molecular modeling and nOe data reveal high interaction complementarity between the mimic and galactoside, similar to natural galectins.

Conclusions:

  • The first synthetic galectin mimic has been successfully designed and synthesized.
  • This mimic effectively replicates the selective binding and interaction complementarity of natural galectins.
  • This breakthrough offers potential for developing new tools in glycobiology and related fields.