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The flexibility-complementarity dichotomy in receptor-ligand interactions.

Hongmei Sun1, Christopher A Hunter1,2, Eva Marina Llamas1

  • 1Department of Chemistry , University of Sheffield , Sheffield S3 7HF , UK .

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|March 22, 2018
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Summary
This summary is machine-generated.

Synthetic supramolecular complexes reveal how molecular structure influences recognition. Ligand flexibility impacts binding affinity, showing a trade-off between preorganization and precise fit for molecular recognition events.

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Area of Science:

  • Supramolecular Chemistry
  • Chemical Biology
  • Molecular Recognition

Background:

  • Synthetic supramolecular complexes enable systematic studies of structure-recognition relationships.
  • Zinc porphyrin-pyridine complexes serve as model systems for exploring molecular recognition.

Purpose of the Study:

  • To investigate the interplay of conformational flexibility and geometric complementarity in molecular recognition.
  • To quantify the impact of intramolecular hydrogen bonds on binding selectivity.

Main Methods:

  • Measured association constants for 48 zinc porphyrin-pyridine complexes in toluene and TCE.
  • Constructed 32 chemical double mutant cycles to analyze free energy contributions.
  • Determined effective molarities (EM) for intramolecular interactions by comparing with intermolecular interactions.

Main Results:

  • Effective molarity (EM) values were solvent-independent and similar for amide and ester acceptors.
  • Ligand linker flexibility significantly varied EM values, with rigid linkers yielding higher EM.
  • Flexible ether linkers showed higher EM than ester linkers, despite conformational penalties.

Conclusions:

  • Ligand preorganization and precise fit are balanced in molecular recognition.
  • Conformational flexibility allows for optimization of geometric complementarity.
  • Understanding these factors is crucial for designing selective molecular recognition systems.