123718-31-0Relevant academic research and scientific papers
All E-10,20-methanoretinoylopsin, light-stable rhodopsin. Synthesis and spectroscopy of all E-10,20-methano- and all-E-retinoyl fluoride and their reaction with bovine opsin
Steen, R. van der,Groesbeek, M.,Amsterdam, L. J. P. van,Lugtenburg, J.,Oostrum, J. van,Grip, W. J. de
, p. 20 - 27 (2007/10/02)
In order to obtain a light-stable rhodopsin as a potential candidate for crystallization and structural X-ray analysis, we synthesized and characterized the novel all E-10,20-methanoretinoyl fluoride (2).This retinal analogue has a locked 11-cis configuration, preventing the light-induced 11-cis -> trans isomerization and binds to opsin by a stable peptide bond rather than a Schiff base. 2 reacted with (methylated) bovine opsin, forming a light- and thermo-stable pigment with λmax at 390 nm.Its opsin shift (2500 cm-1) is in the same order of magnitude as that in rhodopsin (2650 cm-1), suggesting that the mechanism for the red shift is not located in the direct vicinity of the chromophore-protein linkage.We also report the first synthesis and characterization of all-E-retinoyl fluoride (10), which failed to give a pigment on reaction with bovine opsin.
