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Azobenzene as Conformational Switch in Model Peptides
Author(s) -
Renner Christian,
Moroder Luis
Publication year - 2006
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200500531
Subject(s) - azobenzene , photoswitch , isomerization , molecular switch , chemistry , folding (dsp implementation) , conformational change , photoisomerization , molecule , molecular dynamics , biophysics , photochemistry , stereochemistry , computational chemistry , organic chemistry , electrical engineering , biology , engineering , catalysis
The photoinduced isomerization of azobenzene between the extended ( trans ) and compact ( cis ) conformations is reversibly triggered by light of two differing wavelengths. The resulting changes in molecular geometry have been extensively utilized to photoswitch transformations in chemical species reversibly for applications in optoelectronic devises as well as to photocontrol conformational states in (bio)polymers. The high isomerization yield, remarkable photostability and ultrafast kinetics (few ps) of azobenzene are well suited for the design of small, defined model systems that allow detailed folding studies to be carried out both experimentally and theoretically on the same molecules. In our and other laboratories such systems were recently obtained with cyclic peptides of defined conformational preferences as well as with α‐helical and β ‐hairpin peptides. These should, by comparison of simulation and experiment, permit an assessment and improvement of the theoretical description on the one hand and a detailed interpretation of the ultrafast conformational dynamics on the other. The phototriggered changes in conformational states lead to concurrent changes in biophysical properties that can be exploited in the photocontrol of biochemical and biological events, as exemplarily discussed with redox‐active cyclic bis‐cysteinyl peptides and receptor ligands.