title: Chemistry and folding of photomodulable peptides--stilbene and thioaurone-type candidates for conformational switches.
abstract: 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.
authors.affiliation: Dept. of Medicinal Chemistry, Uppsala University, Box 574, 751 23, Uppsala, Sweden.
authors.forename: Máté
authors.initials: M
authors.lastname: Erdélyi
authors.forename: Miranda
authors.initials: M
authors.lastname: Varedian
authors.forename: Christian
authors.initials: C
authors.lastname: Sköld
authors.forename: Ida B
authors.initials: IB
authors.lastname: Niklasson
authors.forename: Johanna
authors.initials: J
authors.lastname: Nurbo
authors.forename: Asa
authors.initials: A
authors.lastname: Persson
authors.forename: Jonas
authors.initials: J
authors.lastname: Bergquist
authors.forename: Adolf
authors.initials: A
authors.lastname: Gogoll
mesh_terms: 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
chemical_list: D001572:Benzofurans; D010455:Peptides; D013267:Stilbenes; C486837:aurone