Synthesis and characterization of a long, rigid photoswitchable cross-linker for promoting peptide and protein conformational change

Chembiochem : a European Journal of Chemical Biology
Fuzhong ZhangG Andrew Woolley

Abstract

Azobenzene-based photoswitchable compounds can be use to photocontrol a variety of biochemical systems. In some cases, their effectiveness may be limited by the size of the conformational change that the switch undergoes. To produce an azobenzene photoswitch that undergoes a large end-to-end distance change upon isomerization, we synthesized 3,3'-diazene-1,2-diylbis{6-[2-sulfonato-4-(chloroacetylamino)phenylethynyl]benzene sulfonic acid} (DDPBA). This long, rigid, water-soluble, thiol-reactive cross-linker undergoes an end-to-end distance change of approximately 13 A upon isomerization. DDPBA was successfully cross-linked to peptides through cysteine side chains. The photoswitch undergoes trans-to-cis photoisomerization maximally when irradiated at 400 nm, although the efficiency of production of the cis isomer is lower than for simpler azobenzenes. Under steady-state illumination conditions, the percentage of cis form produced increases as temperature increases; approximately 56 % cis is obtained at 60 degrees C. Thermal relaxation occurs with a half-life of approximately 75 min at room temperature. When DDPBA was attached to an alpha-helical peptide with two cysteine residues at i and i+14 positions, an increase in helix cont...Continue Reading

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Apr 26, 2013·Chemical Reviews·Wiktor SzymańskiBen L Feringa
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Oct 1, 2021·Chemical Society Reviews·Jana VolarićBen L Feringa

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