Controlling Biological Activity with Light: Diarylethene‐Containing Cyclic Peptidomimetics | Zendy

Babii Oleg | Zendy; Afonin Sergii | Zendy; Berditsch Marina | Zendy; Reiβer Sabine | Zendy; Mykhailiuk Pavel K. | Zendy; Kubyshkin Vladimir S. | Zendy; Steinbrecher Thomas | Zendy; Ulrich Anne S. | Zendy; Komarov Igor V. | Zendy

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Controlling Biological Activity with Light: Diarylethene‐Containing Cyclic Peptidomimetics

Author(s) -

Babii Oleg,

Afonin Sergii,

Berditsch Marina,

Reiβer Sabine,

Mykhailiuk Pavel K.,

Kubyshkin Vladimir S.,

Steinbrecher Thomas,

Ulrich Anne S.,

Komarov Igor V.

Publication year - 2014

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201310019

Subject(s) - peptidomimetic , diarylethene , chemistry , cyclic peptide , chromophore , gramicidin s , folding (dsp implementation) , stereochemistry , combinatorial chemistry , peptide , gramicidin , photochemistry , photochromism , biochemistry , membrane , electrical engineering , engineering

Photobiological processes in nature are usually triggered by nonpeptidic chromophores or by modified side chains. A system is presented in which the polypeptide backbone itself can be conformationally switched by light. An amino acid analogue was designed and synthesized based on a reversibly photoisomerizable diarylethene scaffold. This analogue was incorporated into the cyclic backbone of the antimicrobial peptide gramicidin S at several sites. The biological activity of the resulting peptidomimetics could then be effectively controlled by ultraviolet/visible light within strictly defined spatial and temporal limits.

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