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Pure Appl. Chem., 1985, Vol. 57, No. 5, pp. 753-762

http://dx.doi.org/10.1351/pac198557050753

The synthesis of 13C-labelled retinals

J. Lugtenburg

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  • Álvarez Rosana, Vaz Belén, Gronemeyer Hinrich, de Lera Ángel R.: Functions, Therapeutic Applications, and Synthesis of Retinoids and Carotenoids. Chem. Rev. 2014, 114, 1. <http://dx.doi.org/10.1021/cr400126u>
  • Furutani Yuji, Okitsu Takashi, Reissig Louisa, Mizuno Misao, Homma Michio, Wada Akimori, Mizutani Yasuhisa, Sudo Yuki: Large Spectral Change due to Amide Modes of a β-Sheet upon the Formation of an Early Photointermediate of Middle Rhodopsin. J. Phys. Chem. B 2013, 117, 3449. <http://dx.doi.org/10.1021/jp308765t>
  • Bench Bennie J., Foulke-Abel Jennifer, Watanabe Coran M. H.: Milk, revealed “silent” chemistry: new mode of cycloretinal synthesis. Mol Biosyst 2011, 7, 162. <http://dx.doi.org/10.1039/c0mb00186d>
  • van der Steen R., Biesheuvel P. L., Lugtenburg J., Erkelens C., Mathies R. A.: 8,16- And 8,18-methanobacteriorhodopsin. Synthesis and spectroscopy of 8,16- and 8,18-methanoretinal and their interaction with bacterioopsin. Recl Trav Chim Pays-Bas 2010, 108, 83. <http://dx.doi.org/10.1002/recl.19891080302>
  • Ahuja Shivani, Eilers Markus, Hirshfeld Amiram, Yan Elsa C. Y., Ziliox Martine, Sakmar Thomas P., Sheves Mordechai, Smith Steven O.: 6-s-cis Conformation and Polar Binding Pocket of the Retinal Chromophore in the Photoactivated State of Rhodopsin. J Am Chem Soc 2009, 131, 15160. <http://dx.doi.org/10.1021/ja9034768>
  • Gross Ruth, Wolf Matthias M. N., Schumann Christian, Friedman Noga, Sheves Mordechai, Li Lin, Engelhard Martin, Trentmann Oliver, Neuhaus H. Ekkehard, Diller Rolf: Primary Photoinduced Protein Response in Bacteriorhodopsin and Sensory Rhodopsin II. J Am Chem Soc 2009, 131, 14868. <http://dx.doi.org/10.1021/ja904218n>
  • Bovee-Geurts Petra H. M., Fernández Fernández Isabelle, Liu Robert S. H., Mathies Richard A., Lugtenburg Johan, DeGrip Willem J.: Fluoro Derivatives of Retinal Illuminate the Decisive Role of the C12-H Element in Photoisomerization and Rhodopsin Activation. J Am Chem Soc 2009, 131, 17933. <http://dx.doi.org/10.1021/ja907577p>
  • Ahuja Shivani, Hornak Viktor, Yan Elsa C Y, Syrett Natalie, Goncalves Joseph A, Hirshfeld Amiram, Ziliox Martine, Sakmar Thomas P, Sheves Mordechai, Reeves Philip J: Helix movement is coupled to displacement of the second extracellular loop in rhodopsin activation. Nat Struct Mol Biol 2009, 16, 168. <http://dx.doi.org/10.1038/nsmb.1549>
  • Brown Michael F., Martínez-Mayorga Karina, Nakanishi Koji, Salgado Gilmar F. J., Struts Andrey V.: Retinal Conformation and Dynamics in Activation of Rhodopsin Illuminated by Solid-state 2H NMR Spectroscopy. Photchem Photbio 2009, 85, 442. <http://dx.doi.org/10.1111/j.1751-1097.2008.00510.x>
  • Yamano Yumiko, Ito Masayoshi, Wada Akimori: Total synthesis of cucurbitaxanthin A, cycloviolaxanthin and capsanthin 3,6-epoxide by applying a regioselective ring opening of tetrasubstituted epoxides. Org Biomol Chem 2008, 6, 3421. <http://dx.doi.org/10.1039/b807482h>
  • Brown Michael F., Heyn Maarten P., Job Constantin, Kim Suhkmann, Moltke Stephan, Nakanishi Koji, Nevzorov Alexander A., Struts Andrey V., Salgado Gilmar F.J., Wallat Ingrid: Solid-State 2H NMR spectroscopy of retinal proteins in aligned membranes. Biochim Biophys Acta Biomembr 2007, 1768, 2979. <http://dx.doi.org/10.1016/j.bbamem.2007.10.014>
  • Martínez-Mayorga Karina, Brown Michael F., Nakanishi Koji, Tanaka Katsunori, Struts Andrey V., Krane Sonja, Fujioka Naoko, Salgado Gilmar F. J.: Synthesis of CD3-Labeled 11-cis-Retinals and Application to Solid-State Deuterium NMR Spectroscopy of Rhodopsin. Bull Chem Soc Jpn 2007, 80, 2177. <http://dx.doi.org/10.1246/bcsj.80.2177>
  • Crocker Evan, Eilers Markus, Ahuja Shivani, Hornak Viktor, Hirshfeld Amiram, Sheves Mordechai, Smith Steven O.: Location of Trp265 in Metarhodopsin II: Implications for the Activation Mechanism of the Visual Receptor Rhodopsin. Journal of Molecular Biology 2006, 357, 163. <http://dx.doi.org/10.1016/j.jmb.2005.12.046>
  • Verhoeven Michiel A., Bovee-Geurts Petra H.M., de Groot Huub J.M., Lugtenburg Johan, DeGrip Willem J.: Methyl Substituents at the 11 or 12 Position of Retinal Profoundly and Differentially Affect Photochemistry and Signalling Activity of Rhodopsin. Journal of Molecular Biology 2006, 363, 98. <http://dx.doi.org/10.1016/j.jmb.2006.07.039>
  • Patel A. B., Crocker E., Eilers M., Hirshfeld A., Sheves M., Smith S. O.: Coupling of retinal isomerization to the activation of rhodopsin. Proceedings of the National Academy of Sciences 2004, 101, 10048. <http://dx.doi.org/10.1073/pnas.0402848101>
  • Cia D: A reversed-phase high-performance liquid chromatographic method to analyze retinal isomers. J Chromatogr A 1999, 864, 257. <http://dx.doi.org/10.1016/S0021-9673(99)01024-9>
  • Verdegem Peter J.E., Monnee Menno C.F., Mulder Patrick P.J., Lugtenburg Johan: Condensation of all-E-retinal. Tetrahetron Lett 1997, 38, 5355. <http://dx.doi.org/10.1016/S0040-4039(97)01171-4>
  • Groesbeek M., Lugtenburg J.: SYNTHESIS OF DOUBLY AND MULTIPLY ISOTOPICALLY LABELED RETINALS. Photchem Photbio 1992, 56, 903. <http://dx.doi.org/10.1111/j.1751-1097.1992.tb09711.x>
  • Smith Steven O., Groot Huub de, Gebhard Ronald, Lugtenburg Johan: MAGIC ANGLE SPINNING NMR STUDIES ON THE METARHODOPSIN II INTERMEDIATE OF BOVINE RHODOPSIN: EVIDENCE FOR AN UNPROTONATED SCHIFF BASE. Photchem Photbio 1992, 56, 1035. <http://dx.doi.org/10.1111/j.1751-1097.1992.tb09726.x>
  • Sasaki Jun, Maeda Akio, Shichida Yoshinori, Groesbeek Michel, Lugtenburg Johan, Yoshizawa Tôru: STRUCTURE OF HYPSORHODOPSIN: ANALYSIS BY FOURIER TRANSFORM INFRARED SPECTROSCOPY AT 10 K. Photchem Photbio 1992, 56, 1063. <http://dx.doi.org/10.1111/j.1751-1097.1992.tb09730.x>
  • Fahmy Karim, Siebert Friedrich: THE PHOTOREACTION OF THE DEIONIZED FORM OF THE PURPLE MEMBRANE INVESTIGATED BY FTIR DIFFERENCE SPECTROSCOPY. Photchem Photbio 1990, 51, 459. <http://dx.doi.org/10.1111/j.1751-1097.1990.tb01737.x>
  • Lugtenburg Johan, Mathies Richard A., Griffin Robert G., Herzfeld Judith: Structure and function of rhodopsins from solid state NMR and resonance Raman spectroscopy of isotopic retinal derivatives. Trends Biochem Sci 1988, 13, 388. <http://dx.doi.org/10.1016/0968-0004(88)90181-8>