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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.