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Molecular Tweezers with Additional Recognition Sites.

Christian Heid1, Andrea Sowislok1, Torsten Schaller1

  • 1Faculty of Chemistry, University of Duisburg-Essen, Universitätsstr. 7, 45117, Essen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 18, 2018
PubMed
Summary

Researchers developed new synthetic methods for molecular tweezers, versatile tools for chemical biology. These novel structures with clickable alkynyl phosphates can bind amino acids and peptides.

Keywords:
alkynolsamino acidsestersmolecular tweezerspeptides

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Chemical Biology

Background:

  • Molecular tweezers are crucial host molecules in supramolecular chemistry.
  • Developing versatile synthetic routes for functionalized molecular tweezers is essential for expanding their applications.

Purpose of the Study:

  • To present novel synthetic strategies for molecular tweezers with aliphatic phosphate ester groups.
  • To enable the attachment of functional units via click chemistry for broader applications.

Main Methods:

  • Trichloroacetonitrile method: Activation of hydroxyl groups via trichloroacetimidate intermediates.
  • Phosphoramidite strategy: Activation of hydroquinone precursors followed by coupling and oxidation.
  • Both methods utilize mild conditions for synthesis.

Main Results:

  • Successful synthesis of mono- and disubstituted molecular tweezers.
  • Introduction of alkynyl ester groups for click chemistry functionalization.
  • Demonstrated binding of lysine, arginine, and peptides by the synthesized tweezers.

Conclusions:

  • The developed synthetic routes provide convenient access to novel molecular tweezers.
  • Clickable alkynyl phosphates enhance the versatility of molecular tweezers for chemical biology.
  • The synthetic concept is transferable to other macrocyclic host classes.