Amber Light Control of Peptide Secondary Structure by a Perfluoroaromatic Azobenzene Photoswitch

When amber means “go”: A perfluorinated azobenzene was synthesized and stapled to free cysteines within a helical peptide by using site-selective perfluoroarylation chemistry. Illumination experiments proved successful change of the peptide's secondary structure in response to amber light.

Abstract

The incorporation of photoswitches into the molecular structure of peptides and proteins enables their dynamic photocontrol in complex biological systems. Here, a perfluorinated azobenzene derivative triggered by amber light was site-specifically conjugated to cysteines in a helical peptide by perfluoroarylation chemistry. In response to the photoisomerization (trans→cis) of the conjugated azobenzene with amber light, the secondary structure of the peptide was modulated from a disorganized into an amphiphilic helical structure.

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