A new tool in peptide engineering: a photoswitchable stilbene-type beta-hairpin mimetic.
Peptide secondary structure mimetics are important tools in medicinal chemistry, as they provide analogues of endogenous peptides with new physicochemical and pharmacological properties. The development, synthesis, photochemical investigation, and conformational analysis of a stilbene-type beta-hairpin mimetic capable of light-triggered conformational changes have been achieved. In addition to standard spectroscopic techniques (nuclear Overhauser effects, amide temperature coefficients, circular dichroism spectroscopy), the applicability of self-diffusion measurements (longitudinal eddy current delay pulsed-field gradient spin echo (LED-PGSE) NMR technique) in conformational studies of oligopeptides is demonstrated. The title compound shows photoisomerization of the stilbene chromophore, resulting in a change in solution conformation between an unfolded structure and a folded beta-hairpin.
Erdélyi
Máté
M
Department of Chemistry, Organic Chemistry, Uppsala University, Box 599, 751 24 Uppsala, Sweden.
Karlén
Anders
A
Gogoll
Adolf
A
D040761:Biomimetic Materials / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D002942:Circular Dichroism; D007536:Isomerism; D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D010777:Photochemistry / Q000379:methods*; D011487:Protein Conformation / Q000528:radiation effects; D015202:Protein Engineering / Q000379:methods*; D017433:Protein Structure, Secondary / Q000528:radiation effects*; D013267:Stilbenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects
D009842:Oligopeptides; D013267:Stilbenes