Direct Construction of Corrole-Peptide Conjugates by Controllable Bilane Formation on Resin

Area of Science:

• Organic Chemistry
• Supramolecular Chemistry
• Bioconjugation Chemistry

Background:

• Corroles offer unique properties compared to porphyrins, driving research interest.
• Existing synthetic routes for functionalized corroles are inefficient and complex, limiting their application in bioconjugation.
• Developing straightforward methods for corrole synthesis is crucial for expanding their use.

Purpose of the Study:

• To establish a highly efficient protocol for synthesizing corrole-peptide conjugates.
• To overcome the limitations of preparing functionalized corrole building blocks for bioconjugation.
• To enable the creation of novel corrole-based molecules for diverse applications.

Main Methods:

• A novel condensation strategy involving -COOH-bearing-dipyrromethane molecules and resin-bound peptide chains with aldehyde groups.
• Direct synthesis of corrole-peptide conjugates without pre-synthesized corrole building blocks.
• Controllable reaction conditions allowing for the incorporation of long (up to 25 residues) bioactive peptide chains.

Main Results:

• Achieved high yields (up to 63%) for corrole-peptide conjugate synthesis.
• Produced desired products with minimal purification (at most one chromatographic step).
• Demonstrated the versatility of the method for creating conjugates with long and bioactive peptide sequences.

Conclusions:

• The developed protocol offers an efficient and streamlined approach to corrole-peptide conjugate synthesis.
• These novel conjugates show promise for applications including metal ion chelation in biomedicine, supramolecular materials, and targeted fluorescent probes.
• This work facilitates the broader exploration of corrole derivatives in various scientific fields.