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Pathway Description
11-cis-3-Hydroxyretinal Biosynthesis
Drosophila melanogaster
Metabolic Pathway
(3S)-11-cis-3-hydroxyretinal is one of three chromophores, which then associate with rhodopsins. Specifically, this chromophore associates with the Rh1 rhodopsin, a blue/green sensitive visual pigment found in 6 of the 8 photoreceptor cells in Drosophila melanogaster.
The production of this chromophore begins with zeaxanthin obtained from Drosophila’s dietary sources. This lipid is broken down into (3R)-11-cis-3-hydroxyretinal and (3R)-all-trans-3-hydroxyretinal by a carotenoid isomerooxygenase. The (3R)-cis-3-hydroxyretinal is then attached to a retinoid binding protein, and this complex goes on to be used in the visual cycle of the organism. However, (3R)-all-trans-3-hydroxyretinal must be further processed. It too binds to a retinoid binding protein that will remain unchanged through the rest of the reactions. First, this complex will have a hydrogen added by a photoreceptor dehydrogenase in order to form (3R)-all-trans-3-hydroxyretinol, and then a photoreceptor epimerase will invert its stereochemistry to form (3S)-all-trans-3-hydroxyretinol. From here, an unknown protein, an oxidoreductase that transposes C=C bonds, will form (3S)-11-cis-3-hydroxyretinol. Finally, another photoreceptor dehydrogenase removes a hydrogen from that complex, forming the final product, (3S)-11-cis-3-hydroxyretinal. This complex then joins (3R)-11-cis-3-hydroxyretinal in the visual cycle.
References
11-cis-3-Hydroxyretinal Biosynthesis References
Ahmad ST, Joyce MV, Boggess B, O'Tousa JE: The role of Drosophila ninaG oxidoreductase in visual pigment chromophore biogenesis. J Biol Chem. 2006 Apr 7;281(14):9205-9. doi: 10.1074/jbc.M510293200. Epub 2006 Feb 7.
Pubmed: 16464863
Goldsmith TH, Marks BC, Bernard GD: Separation and identification of geometric isomers of 3-hydroxyretinoids and occurrence in the eyes of insects. Vision Res. 1986;26(11):1763-9.
Pubmed: 3617517
Chou WH, Hall KJ, Wilson DB, Wideman CL, Townson SM, Chadwell LV, Britt SG: Identification of a novel Drosophila opsin reveals specific patterning of the R7 and R8 photoreceptor cells. Neuron. 1996 Dec;17(6):1101-15.
Pubmed: 8982159
Wang X, Wang T, Ni JD, von Lintig J, Montell C: The Drosophila visual cycle and de novo chromophore synthesis depends on rdhB. J Neurosci. 2012 Mar 7;32(10):3485-91. doi: 10.1523/JNEUROSCI.5350-11.2012.
Pubmed: 22399771
Wang T, Montell C: Rhodopsin formation in Drosophila is dependent on the PINTA retinoid-binding protein. J Neurosci. 2005 May 25;25(21):5187-94. doi: 10.1523/JNEUROSCI.0995-05.2005.
Pubmed: 15917458
Wang X, Wang T, Jiao Y, von Lintig J, Montell C: Requirement for an enzymatic visual cycle in Drosophila. Curr Biol. 2010 Jan 26;20(2):93-102. doi: 10.1016/j.cub.2009.12.022. Epub 2009 Dec 31.
Pubmed: 20045325
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