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Synthesis and Mass Spectrometry Analysis of Oligo-peptoids
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Published on: February 21, 2018

Peptoid atropisomers.

Bishwajit Paul1, Glenn L Butterfoss, Mikki G Boswell

  • 1Department of Chemistry, New York University, New York, New York 10003, USA.

Journal of the American Chemical Society
|June 4, 2011
PubMed
Summary
This summary is machine-generated.

Researchers developed N-aryl peptoid oligomers with axial chirality, enabling stable, separable forms. This breakthrough offers a novel method for controlling foldamer conformation and structure.

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Solid-phase Submonomer Synthesis of Peptoid Polymers and their Self-Assembly into Highly-Ordered Nanosheets

Published on: November 2, 2011

Area of Science:

  • Organic Chemistry
  • Polymer Science
  • Chemical Crystallography

Background:

  • Foldamers are synthetic polymers that mimic protein secondary structures.
  • Controlling the conformational stability and chirality of foldamers is crucial for their applications.
  • N-aryl peptoids are a class of foldamers with potential for diverse structural motifs.

Purpose of the Study:

  • To isolate and characterize N-aryl peptoid oligomers exhibiting axial chirality.
  • To investigate the rotational energy barriers around the stereogenic carbon-nitrogen bond.
  • To explore a new strategy for inducing conformational ordering in foldamer compounds.

Main Methods:

  • Synthesis of N-aryl peptoid monomers with ortho-substituted N-aryl side chains.
  • Computational modeling to study atropisomerism.
  • Nuclear Magnetic Resonance (NMR) spectroscopy.
  • X-ray crystallography.
  • High-Performance Liquid Chromatography (HPLC) for separation of atropisomers.
  • Circular Dichroism (CD) spectroscopy.

Main Results:

  • Isolation of N-aryl peptoid oligomers that adopt chiral folds without traditional chiral centers.
  • Identification of monomers exhibiting axial chirality due to restricted rotation around the C-N bond.
  • Demonstration of significant energy barriers to rotation, enabling purification of stable atropisomeric forms.
  • Detailed structural and conformational analysis using a combination of computational and experimental techniques.

Conclusions:

  • N-aryl peptoid oligomers can achieve axial chirality, leading to stable, separable atropisomers.
  • This discovery provides a new method for controlling the conformational properties of foldamers.
  • The findings open avenues for designing novel foldamer-based materials and catalysts.