RSC Publishing


Publishing

 

Cover image for Organic & Biomolecular Chemistry, select for current issue

Organic & Biomolecular Chemistry

The international home of synthetic, physical and biomolecular organic chemistry.



Subscribers

Non-subscribers

Free access



Paper

Org. Biomol. Chem., 2008, 6, 4356 - 4373, DOI: 10.1039/b812001c

Chemistry and folding of photomodulable peptides – stilbene and thioaurone-type candidates for conformational switches

Máté Erdélyi, Miranda Varedian, Christian Sköld, Ida B. Niklasson, Johanna Nurbo, Ĺsa Persson, Jonas Bergquist and Adolf Gogoll

Optimized synthetic strategies for the preparation of photoswitchable molecular scaffolds based on stilbene or on thioaurone chromophores and their conformationally directing properties, as studied by computations and by NMR spectroscopy, are addressed. For the stilbene peptidomimetics 1, 2 and 3, the length of connecting linkers between the chromophore and the peptide strands was varied, resulting in photochromic dipeptidomimetics with various flexibility. Building blocks of higher rigidity, based on para-substituted thioaurone ( 4 and 6) and meta-substituted thioaurone chromophores ( 5 and 7) are shown to have a stronger conformationally directing effect. Design, synthesis, theoretical and experimental conformational analyses are presented.

Graphical abstract image for this article (ID: b812001c)