Chemistry and folding of photomodulable peptides--stilbene and thioaurone-type candidates for conformational switches.
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.
Erdélyi
Máté
M
Dept. of Medicinal Chemistry, Uppsala University, Box 574, 751 23, Uppsala, Sweden.
Varedian
Miranda
M
Sköld
Christian
C
Niklasson
Ida B
IB
Nurbo
Johanna
J
Persson
Asa
A
Bergquist
Jonas
J
Gogoll
Adolf
A
D001572:Benzofurans / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010455:Peptides / Q000737:chemistry* / Q000378:metabolism / Q000528:radiation effects*; D010777:Photochemistry; D011487:Protein Conformation / Q000528:radiation effects; D017510:Protein Folding / Q000528:radiation effects*; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects
D001572:Benzofurans; D010455:Peptides; D013267:Stilbenes; C486837:aurone