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Related Concept Videos

Protein Folding01:22

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Protein Folding01:25

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Proteins are chains of amino acids linked together by peptide bonds. Upon synthesis, a protein folds into a three-dimensional conformation, critical to its biological function. Interactions between its constituent amino acids guide protein folding, and hence the protein structure is primarily dependent on its amino acid sequence.
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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Cavity-containing, backbone-rigidified foldamers and macrocycles.

Kazuhiro Yamato1, Mark Kline, Bing Gong

  • 1Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, NY 14260, USA.

Chemical Communications (Cambridge, England)
|October 30, 2012
PubMed
Summary

Researchers have developed foldamers and macrocycles with defined shapes and cavities using hydrogen-bonding interactions. These molecules form self-assembling nanotubular structures and transmembrane channels with high conductance.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Recent advances in foldamer and macrocycle design have yielded molecules with well-defined shapes and non-deformable cavities.
  • The development of porous molecular structures is a key area of research.

Purpose of the Study:

  • To review the development of foldamers and macrocycles with tunable cavities over the last decade.
  • To highlight a strategy for enforcing folding in unnatural aromatic oligoamide strands using hydrogen-bonding interactions.
  • To explore the application of this folding principle in creating porous structures and self-assembling materials.

Main Methods:

  • Utilizing a robust three-center (bifurcated) hydrogen-bonding interaction to enforce folding of aromatic oligoamide strands.
  • Designing crescent and helical conformations with non-collapsible cavities of tunable diameters.
  • Extending folding principles to aromatic polyamides for a one-pot macrocyclization process.
  • Investigating guest binding properties with guanidinium and octylguanidinium ions.
  • Analyzing self-assembly into nanotubular structures and transmembrane channels.

Main Results:

  • Creation of aromatic oligoamides with crescent and helical conformations and tunable cavities.
  • Discovery of a highly efficient one-pot macrocyclization process for aromatic polyamides, amides, hydrazides, and ureas.
  • Demonstration that macrocycle formation efficiency is enhanced by precursor folding.
  • Oligoamide macrocycles and crescent oligoamides exhibit tunable selectivity for binding guests like guanidinium ions.
  • Rigid macrocycles form directional aggregates, leading to nanotubular assemblies with fixed-size pores.
  • Oligoamide macrocycles self-assemble into high-conductance transmembrane channels.

Conclusions:

  • A robust strategy based on hydrogen bonding enables the design of foldamers and macrocycles with predictable shapes and cavities.
  • These molecules can be efficiently synthesized and exhibit tunable guest binding properties.
  • The self-assembly of these rigid macrocycles into nanotubular structures and transmembrane channels opens possibilities for advanced materials and nanotechnology.