Photomodulation of conformational states. III. Water-soluble bis-cysteinyl-peptides with (4-aminomethyl) phenylazobenzoic acid as backbone constituent

Biopolymers
C RennerL Moroder

Abstract

In previous studies we have shown that light-induced cis/trans isomerization of the azobenzene moiety in cyclo-[Ala-Cys-Ala-Thr-Cys-Asp-Gly-Phe-AMPB] [AMPB: (4-aminomethyl)phenylazobenzoic acid] leads both in the monocyclic and in the oxidized bicyclic form to markedly differentiated conformational states in DMSO, a fact that lends itself for photomodulation of the redox potential of such bis-cysteinyl-peptides. For this purpose water-soluble systems are required, and this was achieved by replacing three residues outside the Cys-Ala-Thr-Cys active-site motif of thioredoxin reductase with lysines. The resulting cyclo-[Lys-Cys-Ala-Thr-Cys-Asp-Lys-Lys-AMPB] fully retains its photoresponsive properties in water as well assessed by uv and CD measurements. Paralleling results of the previously investigated azobenzene-containing cyclic peptides, the trans --> cis isomerization of the water-soluble monocyclic and oxidized bicyclic peptide is accompanied by a marked transition from a well-defined conformation to an ensemble of possible conformations. However, the conformational preferences are very dissimilar from those of the DMSO-soluble peptides. In fact, hydrogen bonds as well as secondary structure elements were found that change i...Continue Reading

References

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Citations

Apr 26, 2013·Chemical Reviews·Wiktor SzymańskiBen L Feringa
Feb 3, 2005·The Journal of Peptide Research : Official Journal of the American Peptide Society·C RennerL Moroder
Dec 16, 2011·The Journal of Chemical Physics·Maja KobusGerhard Stock
Dec 17, 2008·Organic & Biomolecular Chemistry·Rolf PfisterChristoph Kolano
Mar 23, 2005·Journal of Peptide Science : an Official Publication of the European Peptide Society·Luis Moroder
Apr 28, 2006·Chembiochem : a European Journal of Chemical Biology·Christian Renner, Luis Moroder
Dec 19, 2008·Journal of Peptide Science : an Official Publication of the European Peptide Society·Miranda VaredianAdolf Gogoll
Jan 3, 2006·Biophysical Journal·Markus LöweneckChristian Renner
Sep 28, 2005·Chemistry : a European Journal·Máté ErdélyiAdolf Gogoll
Jul 3, 2003·Chemistry & Biology·Markus SchüttLuis Moroder
Aug 20, 2016·Chemical Communications : Chem Comm·Robert J Mart, Rudolf K Allemann
Aug 15, 2019·Chemical Communications : Chem Comm·Lea Albert, Olalla Vázquez
Aug 14, 2020·Chemical Reviews·Rasha JwadLuke Hunter
Aug 19, 2007·The Journal of Physical Chemistry. B·Florian O KollerWolfgang Zinth
Jan 1, 2006·Journal of Chemical Theory and Computation·Marc FuhrmansChristian Renner
Sep 24, 2011·The Journal of Physical Chemistry. B·Phuong H NguyenGerhard Stock
Jul 10, 2003·Chemical Reviews·Christophe Dugave, Luc Demange
Oct 10, 2006·The Journal of Organic Chemistry·Robert F Standaert, Seung Bum Park

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