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A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...
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Self-Assembling Cyclic Peptide Cylinders as Nuclei for Crystal Engineering.

Dennis T Bong1, M Reza Ghadiri1

  • 1Departments of Chemistry and Molecular Biology and The Skaggs Institute for Chemical Biology The Scripps Research Institute 10550 N. Torrey Pines Road La Jolla, CA 92037 (USA) Fax: (+1) 858-784-2798.

Angewandte Chemie (International Ed. in English)
|May 2, 2018
PubMed
Summary
This summary is machine-generated.

Cyclic D,L-peptides self-assemble to create supramolecular recognition interfaces. Phenyl-phenyl interactions guide the organization of these peptide dimers, suggesting their utility in crystal engineering applications.

Keywords:
crystal engineeringnanostructurespeptidespi interactionsself-assembly

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Area of Science:

  • Supramolecular Chemistry
  • Peptide Chemistry
  • Crystal Engineering

Background:

  • Self-assembly of cyclic peptides can form novel interfaces.
  • Understanding molecular interactions is key to designing ordered structures.

Purpose of the Study:

  • To investigate the self-assembly of cyclic D,L-peptides.
  • To elucidate the role of phenyl-phenyl interactions in solid-state organization.
  • To explore the potential of these peptides in crystal engineering.

Main Methods:

  • Synthesis and characterization of dimeric peptide cyclo[(-L-Phe-D-Me N-Ala-L-hPhe-D-Me N-Ala)2] (1).
  • Analysis of solid-state organization using crystallographic methods.
  • Investigation of phenyl-phenyl interactions driving self-assembly.

Main Results:

  • A supramolecular recognition interface was successfully formed via self-assembly.
  • Phenyl-phenyl interactions were identified as the primary drivers of solid-state organization.
  • Dimeric peptide 1 forms clusters through edge-to-face contacts.

Conclusions:

  • Cyclic D,L-peptides can self-assemble into functional supramolecular interfaces.
  • The observed organization is directed by specific phenyl-phenyl interactions.
  • These peptide scaffolds show promise as building blocks for crystal engineering.