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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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Chloride-Assisted Peptide Macrocyclization.

Nikolina Vidović1, Gordan Horvat2, Davide Riva1

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Summary

Chloride anions act as effective templates in cyclopeptide synthesis, significantly improving yields compared to traditional cation-promoted methods. This anion-assisted approach enables the successful synthesis of complex cyclic peptides.

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Area of Science:

  • Organic Chemistry
  • Peptide Chemistry
  • Synthetic Chemistry

Background:

  • Cyclic peptides are important biomolecules with diverse applications.
  • Traditional synthesis methods often face challenges with yield and efficiency.
  • The templating effect of ions in cyclization is an area of interest.

Purpose of the Study:

  • To investigate the role of the chloride (Cl-) anion as a templating agent in cyclopeptide synthesis.
  • To compare the efficiency of chloride-templating with cation-promoted cyclization methods.
  • To synthesize novel homocyclolysines and other cyclic peptides.

Main Methods:

  • Head-to-tail lactamization was employed for cyclic peptide formation.
  • Synthesis was performed using a chloride-templating approach.
  • A cation-promoted procedure was used for comparative analysis.

Main Results:

  • Isolated yields were considerably higher using the chloride-templating approach.
  • The anion-assisted synthesis successfully produced desired cyclopeptides where cation-promoted methods failed.
  • Three new homocyclolysines and six other cyclic peptides were synthesized.

Conclusions:

  • Chloride anions serve as effective templates for cyclopeptide synthesis.
  • The chloride-templating method offers a superior alternative to cation-promoted procedures for yield and success rate.
  • This strategy facilitates the synthesis of challenging cyclic peptide structures.