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Related Experiment Videos

Cyclic peptoids.

Sung Bin Y Shin1, Barney Yoo, Louis J Todaro

  • 1Department of Chemistry, New York University, 100 Washington Square East, New York, New York 10003-6688, USA.

Journal of the American Chemical Society
|February 28, 2007
PubMed
Summary
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N-substituted glycine oligomers, or peptoids, efficiently form head-to-tail macrocycles. This covalent constraint enhances folding, enabling crystallization and revealing novel reverse-turn structures in peptoid macrocycles.

Area of Science:

  • Biomimetic chemistry
  • Supramolecular chemistry
  • Polymer science

Background:

  • Foldamers are biomimetic oligomers known for stable secondary structures.
  • N-substituted glycine oligomers (peptoids) mimic polyproline type I helices.
  • Research aims to enhance peptoid folding stability and discover new structural motifs.

Purpose of the Study:

  • To investigate head-to-tail macrocyclization reactions in peptoids.
  • To explore the impact of macrocyclization on peptoid conformational stability.
  • To determine the structural characteristics of cyclic peptoid hetero-oligomers.

Main Methods:

  • Synthesis of diverse peptoid sequences (pentamers to 20mers).
  • Head-to-tail macrocyclization reactions under mild conditions (room temperature, 5 min).

Related Experiment Videos

  • X-ray crystallography of cyclic peptoid hexamers and octamers.
  • Main Results:

    • Highly efficient head-to-tail macrocyclization of peptoids achieved.
    • Macrocyclization significantly enhanced conformational ordering.
    • First X-ray crystallographic structures of cyclic peptoid hetero-oligomers obtained.
    • Revealed formation of reverse-turn conformations in peptoid macrocycles.

    Conclusions:

    • Peptoid macrocyclization is a facile and efficient method for creating constrained foldamers.
    • Macrocyclic constraint promotes ordered structures, facilitating crystallization.
    • Peptoid macrocycles can adopt reverse-turn conformations, expanding the repertoire of foldamer structures.