Chemistry and folding of photomodulable peptides: stilbene and thioaurone-type candidates for conformational switches
2008 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 6, no 23, 4356-4373 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
2008. Vol. 6, no 23, 4356-4373 p.
Pharmaceutical Sciences Chemical Sciences
IdentifiersURN: urn:nbn:se:uu:diva-97699DOI: 10.1039/b812001cISI: 000261744800012PubMedID: 19005595OAI: oai:DiVA.org:uu-97699DiVA: diva2:172739