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- W2095693359 abstract "Abstract The visual pigment rhodopsin, the photosensory element of the rod photoreceptor cell in the vertebrate retina, shows in combination with an endogenous ligand, 11‐ Z retinal, an astonishing photochemical performance. It exhibits an unprecedented quantum yield (0.67) in a highly defined and ultrafast photoisomerization process. This triggers the conformational changes leading to the active state Meta(rhodopsin) II. Retinal is covalently bound to Lys‐296 of the protein opsin in a protonated Schiff base. The resulting positive charge delocalization over the terminal part of the polyene chain of retinal creates a conjugation defect that upon photoexcitation moves to the opposite end of the polyene. Shortening the polyene as in 4,5‐dehydro,5,6‐dihydro (alpha), 5,6‐dihydro or 7,8‐dihydro‐analogs might facilitate photoisomerization of a 9‐ Z and a 11‐ Z bond. Here we describe pigment analogs generated with bovine opsin and 11‐ Z or 9‐ Z 4,5‐dehydro,5,6‐dihydro‐retinal that were further characterized by UV–Vis and FTIR spectroscopy. The preference of opsin for native 11‐ Z retinal over the 9‐ Z isomer is reversed in 4,5‐dehydro,5,6‐dihydro‐retinal. 9‐ Z 4,5‐dehydro,5,6‐dihydro‐retinal readily generated a photosensitive pigment. This modification has no effect on the quantum yield, but affects the Batho↔blueshifted intermediate (BSI) equilibrium and leads to a strong decrease in the G‐protein activation rate because of a downshift of the p K a of the Meta I↔Meta II equilibrium." @default.
- W2095693359 created "2016-06-24" @default.
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- W2095693359 date "2008-07-01" @default.
- W2095693359 modified "2023-10-18" @default.
- W2095693359 title "Alpha-retinals as Rhodopsin ChromophoresPreference for the 9-<i>Z</i>Configuration and Partial Agonist Activity<sup />" @default.
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- W2095693359 doi "https://doi.org/10.1111/j.1751-1097.2008.00321.x" @default.
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