Controlling Biological Activity with Light: Diarylethene-Containing Cyclic Peptidomimetics

Authors


  • This manuscript is dedicated to the 72nd anniversary of the antimicrobial peptide gramicidin S discovery. We thank Dr. D. Sysoev for discussions and advice on the synthesis of compound 1. O.B. is grateful to KHYS for a fellowship. Financial assistance from Enamine Ltd. (http://www.enamine.net) is also acknowledged.

Abstract

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.

Ancillary