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Reverse Turn and Loop Secondary Structures in Stereodefined Cyclic Peptoid Scaffolds.

Assunta D'Amato1, Giovanni Pierri1, Consiglia Tedesco1

  • 1Department of Chemistry and Biology "A. Zambelli" , University of Salerno , Via Giovanni Paolo II, 132 , Fisciano , Salerno 84084 Italy.

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Researchers explored cyclic peptoid architectures, revealing noncovalent interactions that stabilize structures and influence backbone order. This work advances the design of stable, stereodefined peptidomimetic foldamers for diverse scientific applications.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Chemical Biology

Background:

  • Controlling intramolecular interactions and amide bond configurations in cyclic peptoids is crucial for stable secondary structures.
  • Designing stable reverse turns and loops in peptidomimetics presents a significant challenge.

Purpose of the Study:

  • To investigate noncovalent interactions stabilizing cyclic peptoids with specific chiral side chains.
  • To understand how these interactions influence backbone topology and secondary structure formation.
  • To explore the potential of asymmetric cyclic peptoids as scaffolds for novel foldamers.

Main Methods:

  • Nuclear Magnetic Resonance (NMR) spectroscopy
  • Single-crystal X-ray crystallography
  • Density Functional Theory (DFT) calculations
  • Analysis of tri-, tetra-, hexa-, and octameric cyclic peptoids

Main Results:

  • Identified key noncovalent interactions stabilizing cyclic peptoids and their host-guest complexes.
  • Disclosed novel gamma- and beta-turn structures in alpha-peptoid macrocycles.
  • Determined the solid-state structure of the largest metallated cyclic peptoid, featuring an alternating cis/trans amide linkage.
  • Demonstrated that elements of asymmetry lead to atroposelective construction and conformational stability.

Conclusions:

  • Strategic placement of chiral side chains and control of amide bond equilibria enable the design of stable cyclic peptoid architectures.
  • These findings provide a minimalist scaffold for stereodefined peptidomimetic foldamers and topologically biased libraries.
  • The study opens avenues for future applications of peptoids across various scientific disciplines.