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Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
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Researchers created stable, porous peptide capsules using dynamic covalent chemistry. These biocompatible structures, inspired by nature, show promise for various applications by controlling side-chain positioning within cavities.

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Area of Science:

  • Supramolecular Chemistry
  • Peptide Self-Assembly
  • Biomaterials Engineering

Background:

  • Peptides are challenging building blocks for porous structures due to flexibility and shape persistence issues.
  • However, peptides offer inherent functionality, biocompatibility, and diversity, making them attractive for advanced materials.
  • Nature-inspired approaches can leverage peptide backbones for structure and side chains for function.

Purpose of the Study:

  • To construct discrete porous peptide-based capsules by preorganizing peptide ribbons on a macrocyclic scaffold.
  • To exploit dynamic covalent chemistry for combinatorial discovery and rational design of self-assembled peptide capsules.
  • To investigate the role of peptide chirality in capsule formation, stability, and internal functionality.

Main Methods:

  • Azapeptide-aldehyde reactions to preorganize peptide ribbons on macrocyclic scaffolds, forming cavitands with semicarbazone linkers.
  • Self-assembly of dimeric capsules mimicking eight-stranded β-barrels through peptide backbone interactions.
  • Dynamic covalent chemistry (DCC) for combinatorial screening and optimization of capsule structures.
  • Circular dichroism (CD) spectroscopy, TD DFT calculations, DOSY, and X-ray crystallography for structural elucidation and stability assessment.

Main Results:

  • Well-defined dimeric capsules were formed, with side chains positioned inside cavities, particularly with (l, d, d) azapeptide sequences.
  • DCC enabled the discovery of stable capsules with internally positioned side chains using shorter peptide sequences and specific chiral combinations ((l, l) and (d, l)).
  • A hybrid (l, l)(d, l) capsule was successfully amplified directly from a mixed reaction solution.
  • Self-assembly significantly enhanced structural ordering, evidenced by a two-order magnitude increase in CD spectra intensity.
  • Peptide capsules demonstrated remarkable thermal stability, remaining intact from 20 °C to 100 °C.

Conclusions:

  • Peptides can be effectively utilized as building blocks for creating stable, functional porous capsules through rational design and DCC.
  • Chirality plays a critical role in directing self-assembly, capsule stability, and the precise positioning of functional side chains.
  • The developed peptide capsules exhibit excellent structural integrity and stability, opening avenues for applications in areas requiring biocompatible porous materials.