- Synthesis of 9-CD3-9-cis-retinal cofactor of isorhodopsin
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We report the synthesis of 9-CD3-9-cis-retinal via a six-step procedure from β-ionone. The steps involve an initial deuteration of the methyl ketone of β-ionone followed by two consecutive Horner-Wadsworth-Emmons (HWE) coupling reactions and th
- Navidi, Mozhgan,Yadav, Shreya,Struts, Andrey V.,Brown, Michael F.,Nesnas, Nasri
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supporting information
p. 4521 - 4524
(2018/11/23)
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- Synthesis of CD3-labeled 11-cis-retinals and application to solid-state deuterium NMR spectroscopy of rhodopsin
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Efficient synthesis of 11-Z-retinals labeled with 2H at the C5, C9, or C13 methyl groups is described. The 2H-labeled retinals were used to regenerate the visual pigment rhodopsin for structural investigations. Solid-state 2H NMR data provided the orientation of retinal within the rhodopsin binding pocket as well as its conformation. Extension of the approach to other membrane receptors can yield knowledge of their mechanisms of activation as a guide for ligand-based drug design.
- Tanaka, Katsunori,Struts, Andrey V.,Krane, Sonja,Fujioka, Naoko,Salgado, Gilmar F. J.,Martinez-Mayorga, Karina,Brown, Michael F.,Nakanishi, Koji
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body text
p. 2177 - 2184
(2009/08/08)
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- Efficient generation of a trisporoid library by combination of synthesis and biotransformation
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(Chemical Equation Presented) Trisporic acids and their biosynthetic precursors represent a family of powerful fungal pheromones and morphogenetic factors. A highly flexible synthetic protocol is described that (i) provides rapid access to nonfunctionaliz
- Schachtschabel, Doreen,Boland, Wilhelm
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p. 1366 - 1372
(2007/10/03)
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- A SHORT PATH SYNTHESIS OF RETINALS. SYNTHESIS OF 13C- OR 2H-LABELED RETINALS
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Trimethylsilylated acetaldehyde t-butylimine 4 was found to be an effective two carbon-homologenation reagent in the synthesis of retinals and its congeners.A short path synthesis of retinals (1 and 2) by using 4 and its application to the synthesis of 13C-labeled retinal 12 and octadeuterium retinal 27 is described.KEYWORDS - retinal; retinoid; vitamin A aldehyde; visual pigment; α,β-unsaturated aldehyde synthesis; silylated imine
- Akita, Hiroyuki
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p. 1796 - 1799
(2007/10/02)
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- Preparation and photolysis of deuterium-labelled rhodopsin analogues
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The compounds 18- and 19-trideutero-11-cis-retinal, > 99percent pure, with over 98percent and 99percent trideuterium incorporation were synthesized together with the corresponding all-trans derivatives.Rhodopsins were prepared from bovine opsin and 18- and 19-trideutero-11-cis-retinal, 18- and 19-trideutero-all-trans-retinal were isolated as oximes after photolysis of the corresponding rhodopsins.The oximes showed the same deuterium incorporation as the starting 18- and 19-trideutero-11-cis-retinals and as those oximes obtained by denaturation of 18- and 19-trideuterorhodopsin in the dark.These results demonstrate that during rhodopsin photolysis no detectable exchange of D or H occurs at carbon atoms 18 and 19.These facts, together with Resonance Raman data of 18-trideutero-bathorhodopsin and 5-demethylbathorhodopsin, establish that the primary step in rhodopsin photochemistry is not a phototautomerization involving the 5-CH3 group.With respect to the possibility that the primary step is a phototautomerization involving the 9-CH3 group, the situation is less clear.At this time experimental evidence of the various research disciplines is insufficiently conclusive to establish unambiguously which of the two possibilities, cis-trans photoisomerization or phototautomerization involving the 9-CH3 group, is the primary event in visual photochemistry.
- Fransen, M. R.,Palings, I.,Lugtenburg, J.,Jansen, P. A. A.,Groenendijk, G. W. T.
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p. 384 - 391
(2007/10/02)
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