Photolysis intermediates of the artificial visual pigment cis-5,6-dihydro-isorhodopsin. 1989

A Albeck, and N Friedman, and M Ottolenghi, and M Sheves, and C M Einterz, and S J Hug, and J W Lewis, and D S Kliger
Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, Israel.

The photolysis intermediates of an artificial bovine rhodopsin pigment, cis-5,6-dihydro-isorhodopsin (cis-5,6,-diH-ISORHO, lambda max 461 nm), which contains a cis-5,6-dihydro-9-cis-retinal chromophore, are investigated by room temperature, nanosecond laser photolysis, and low temperature irradiation studies. The observations are discussed both in terms of low temperature experiments of Yoshizawa and co-workers on trans-5,6-diH-ISORHO (Yoshizawa, T., Y. Shichida, and S. Matuoka. 1984. Vision Res. 24: 1455-1463), and in relation to the photolysis intermediates of native bovine rhodopsin (RHO). It is suggested that in 5,6-diH-ISORHO, a primary bathorhodopsin intermediate analogous to the bathorhodopsin intermediate (BATHO) of the native pigment, rapidly converts to a blue-shifted intermediate (BSI, lambda max 430 nm) which is not observed after photolysis of native rhodopsin. The analogs from lumirhodopsin (LUMI) to meta-II rhodopsin (META-II) are generated subsequent to BSI, similar to their generation from BATHO in the native pigment. It is proposed that the retinal chromophore in the bathorhodopsin stage of 5,6-diH-ISORHO is relieved of strain induced by the primary cis to trans isomerization by undergoing a geometrical rearrangement of the retinal. Such a rearrangement, which leads to BSI, would not take place so rapidly in the native pigment due to ring-protein interactions. In the native pigment, the strain in BATHO would be relieved only on a longer time scale, via a process with a rate determined by protein relaxation.

UI MeSH Term Description Entries
D007536 Isomerism The phenomenon whereby certain chemical compounds have structures that are different although the compounds possess the same elemental composition. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Isomerisms
D010782 Photolysis Chemical bond cleavage reactions resulting from absorption of radiant energy. Photodegradation
D012168 Retinal Pigments Photosensitive protein complexes of varied light absorption properties which are expressed in the PHOTORECEPTOR CELLS. They are OPSINS conjugated with VITAMIN A-based chromophores. Chromophores capture photons of light, leading to the activation of opsins and a biochemical cascade that ultimately excites the photoreceptor cells. Retinal Photoreceptor Pigment,Retinal Pigment,Visual Pigment,Visual Pigments,Retinal Photoreceptor Pigments,Photoreceptor Pigment, Retinal,Photoreceptor Pigments, Retinal,Pigment, Retinal,Pigment, Retinal Photoreceptor,Pigment, Visual,Pigments, Retinal,Pigments, Retinal Photoreceptor,Pigments, Visual
D012243 Rhodopsin A purplish-red, light-sensitive pigment found in RETINAL ROD CELLS of most vertebrates. It is a complex consisting of a molecule of ROD OPSIN and a molecule of 11-cis retinal (RETINALDEHYDE). Rhodopsin exhibits peak absorption wavelength at about 500 nm. Visual Purple
D013053 Spectrophotometry The art or process of comparing photometrically the relative intensities of the light in different parts of the spectrum.
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships

Related Publications

A Albeck, and N Friedman, and M Ottolenghi, and M Sheves, and C M Einterz, and S J Hug, and J W Lewis, and D S Kliger
February 1990, Biochemistry,
A Albeck, and N Friedman, and M Ottolenghi, and M Sheves, and C M Einterz, and S J Hug, and J W Lewis, and D S Kliger
November 1997, Biochemistry,
A Albeck, and N Friedman, and M Ottolenghi, and M Sheves, and C M Einterz, and S J Hug, and J W Lewis, and D S Kliger
May 1995, Biochemistry,
A Albeck, and N Friedman, and M Ottolenghi, and M Sheves, and C M Einterz, and S J Hug, and J W Lewis, and D S Kliger
April 1975, Proceedings of the National Academy of Sciences of the United States of America,
A Albeck, and N Friedman, and M Ottolenghi, and M Sheves, and C M Einterz, and S J Hug, and J W Lewis, and D S Kliger
June 1970, Proceedings of the National Academy of Sciences of the United States of America,
A Albeck, and N Friedman, and M Ottolenghi, and M Sheves, and C M Einterz, and S J Hug, and J W Lewis, and D S Kliger
May 1973, Doklady Akademii nauk SSSR,
A Albeck, and N Friedman, and M Ottolenghi, and M Sheves, and C M Einterz, and S J Hug, and J W Lewis, and D S Kliger
January 1979, Journal of nutritional science and vitaminology,
A Albeck, and N Friedman, and M Ottolenghi, and M Sheves, and C M Einterz, and S J Hug, and J W Lewis, and D S Kliger
February 1983, Photochemistry and photobiology,
A Albeck, and N Friedman, and M Ottolenghi, and M Sheves, and C M Einterz, and S J Hug, and J W Lewis, and D S Kliger
February 2014, Angewandte Chemie (International ed. in English),
A Albeck, and N Friedman, and M Ottolenghi, and M Sheves, and C M Einterz, and S J Hug, and J W Lewis, and D S Kliger
April 1996, The Journal of organic chemistry,
Copied contents to your clipboard!