ArticleJournal of the American Chemical Society2011
Why 11-cis-retinal? Why not 7-cis-, 9-cis-, or 13-cis-retinal in the eye?
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 66 citations in OpenAlex.
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- Bioluminescence and environmental light drive the visual evolution of deep-sea shrimp (Oplophoroidea).Communications biology · 2025Article
- Study of Photoselectivity in Linear Conjugated Chromophores Using the XMS-CASPT2 Method.ACS physical chemistry Au · 2024Article
- Beyond Lux: methods for species and photoreceptor-specific quantification of ambient light for mammals.BMC biology · 2024Article
- Ectopically expressed rhodopsin is not sensitive to X-rays.BMC neuroscience · 2024Article
- Theoretical study on the structure, spectroscopic, and current-voltage behavior of 11-Cis and Trans retinal isomers in rhodopsin.Scientific reports · 2024Article
- Discovering genotype-phenotype relationships with machine learning and the Visual Physiology Opsin Database (VPOD).GigaScience · 2024Article
- Stereoselective synthesis of (RSC advances · 2023Article
- The evolutionary history and spectral tuning of vertebrate visual opsins.Developmental biology · 2023Review
- Molecular advances to study the function, evolution and spectral tuning of arthropod visual opsins.Philosophical transactions of the Royal Society of London. Series B, Biological sciences · 2022Review
- Light environment drives evolution of color vision genes in butterflies and moths.Communications biology · 2021Article
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- Illuminating insights into opsin 3 function in the skin.Advances in biological regulation · 2020Review
- Flavonoid allosteric modulation of mutated visual rhodopsin associated with retinitis pigmentosa.Scientific reports · 2017Article
- Ectopic Expression of Mouse Melanopsin inThe Journal of biological chemistry · 2017Article
- Article
- Molecular bases for the selection of the chromophore of animal rhodopsins.Proceedings of the National Academy of Sciences of the United States of America · 2015Article
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- QM/MM model of the mouse olfactory receptor MOR244-3 validated by site-directed mutagenesis experiments.Biophysical journal · 2014Article
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Authors and funding
2 authors at 1 institution in 2 countries.
Funding
Abstract
One of the basic and unresolved puzzles in the chemistry of vision concerns the natural selection of 11-cis-retinal as the light-sensing chromophore in visual pigments. A detailed computational examination of the structure, stability, energetics, and spectroscopy of 7-cis-, 9-cis-, 11-cis-, and 13-cis-retinal isomers in vertebrate (bovine, monkey) and invertebrate (squid) visual pigments was carried out using a hybrid quantum mechanics/molecular mechanics (QM/MM) method. The results show that the electrostatic interaction between retinal and opsin dominates the natural selection of 11-cis-retinal over other cis isomers in the dark state. In all of the pigments, 9-cis-retinal was found to be only slightly higher in energy than 11-cis-retinal, which provides strong evidence for the presence of 9-cis-rhodopsin in nature. 7-cis-Retinal is suggested to be an "upside-down" version of the all-trans isomer because the structural rearrangements observed for 7-cis-rhodopsin from squid were found to be very similar to those for squid bathorhodopsin. The progressive red shift in the calculated absorption wavelength (λ(max)) (431, 456, 490, and 508 nm for the 7-cis-, 9-cis-, 11-cis-, and 13-cis-retinal isomers) is due to the decrease in bond length alternation of the retinal.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.