259538-59-5Relevant academic research and scientific papers
Photochemical regulation of an artificial hydrolase by a backbone incorporated tertiary structure switch
Lindgren, N. Johan V.,Varedian, Miranda,Gogoll, Adolf
supporting information; experimental part, p. 501 - 505 (2009/07/10)
A stilbene chromophore has been incorporated into the turn region of a 42 amino acid peptide, linking two helical peptide sections. Spatial proximity between these sections, as well as aggregation into dimers, is required to facilitate the catalytic function of this artificial hydrolase. Photomodulation of the hydrolase activity results in an increase of the activity of 42% upon switching from the trans to the cis isomer of the chromophore. This is rationalized by a change in the aggregation state of the peptidomimetic, which is supported by diffusion coefficients obtained from PFG-NMR experiments. The results show that incorporation of a small, relatively flexible chromophore into a large peptide is capable of inducing a considerable change in tertiary structure and thus, functionality.
Chemistry and folding of photomodulable peptides - Stilbene and thioaurone-type candidates for conformational switches
Erdelyi, Mate,Varedian, Miranda,Skoeld, Christian,Niklasson, Ida B.,Nurbo, Johanna,Persson, Asa,Bergquist, Jonas,Gogoll, Adolf
scheme or table, p. 4356 - 4373 (2009/02/07)
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.
Functionalized rubbery polymers
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Page/Page column 10, (2008/06/13)
This invention discloses a functional monomer, its use in a polymer, a rubbery composition, a tire, and a process to make such a rubbery composition. The functional monomer has a structural formula selected from the group consisting of: wherein the R
A new tool in peptide engineering: A photoswitchable stilbene-type β-hairpin mimetic
Erdelyi, Mate,Karlen, Anders,Gogoll, Adolf
, p. 403 - 412 (2008/09/19)
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 stil-bene-type β-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 β-hairpin.
