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Controlling biological activity with light: diarylethene-containing cyclic peptidomimetics
Oleg Babii1, Sergii Afonin, Marina Berditsch
1Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry and CFN, Fritz-Haber-Weg 6, 76131 Karlsruhe (Germany).
Angewandte Chemie (International Ed. in English)
|February 21, 2014
Summary
Scientists developed a novel method to control peptide conformation and biological activity using light. This involves incorporating a photo-switchable amino acid into gramicidin S, enabling light-triggered conformational changes and activity modulation.
Area of Science:
- Photochemistry
- Biochemistry
- Peptide Science
Background:
- Natural photobiological processes typically rely on external chromophores or modified amino acid side chains.
- Controlling peptide conformation and function using light offers precise spatiotemporal regulation.
Purpose of the Study:
- To engineer a system where the polypeptide backbone itself can be conformationally switched by light.
- To demonstrate light-inducible control over the biological activity of a peptide.
Main Methods:
- Design and synthesis of a novel amino acid analogue featuring a photoisomerizable diarylethene scaffold.
- Incorporation of this analogue into the cyclic backbone of the antimicrobial peptide gramicidin S.
- Evaluation of the biological activity of the modified peptides under UV/Visible light irradiation.
Main Results:
- Successful synthesis of a photo-switchable amino acid analogue.
- Demonstrated incorporation of the analogue into gramicidin S without compromising its structure.
- Effective control of the antimicrobial peptide's biological activity using ultraviolet/visible light.
Conclusions:
- The polypeptide backbone can be conformationally switched by light through the incorporation of photoisomerizable amino acid analogues.
- This approach allows for precise spatial and temporal control over peptide biological activity.
- The developed system offers a novel platform for light-regulated peptide therapeutics and molecular tools.

