Synthesis of isotopically labeled all-trans retinals for DNP-enhanced solid-state NMR studies of retinylidene proteins

Journal of Labelled Compounds & Radiopharmaceuticals
Alexander J LeederRichard C D Brown

Abstract

Three all-trans retinals containing multiple 13 C labels have been synthesized to enable dynamic nuclear polarization enhanced solid-state magic angle spinning NMR studies of novel microbial retinylidene membrane proteins including proteorhodpsin and channelrhodopsin. The synthetic approaches allowed specific introduction of 13 C labels in ring substituents and at different positions in the polyene chain to probe structural features such as ring orientation and interaction of the chromophore with the protein in the ground state and in photointermediates. [10-18-13 C9 ]-All-trans-retinal (1b), [12,15-13 C2 ]-all-trans-retinal (1c), and [14,15-13 C2 ]-all-trans-retinal (1d) were synthesized in in 12, 8, and 7 linear steps from ethyl 2-oxocyclohexanecarboxylate (5) or β-ionone (4), respectively.

References

May 26, 2001·Annual Review of Nutrition·C B Stephensen
Jan 28, 2003·Biophysical Journal·György VáróJanos K Lanyi
Jun 8, 2006·Annual Review of Biochemistry·Krzysztof Palczewski
Feb 13, 2008·The Journal of Chemical Physics·Thorsten MalyRobert G Griffin
Jul 23, 2008·Journal of the American Chemical Society·Maria ConcistrèMalcolm H Levitt
Mar 26, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Prativa B S Dawadi, Johan Lugtenburg
Apr 23, 2010·Journal of the American Chemical Society·Sushabhan SadhukhanGregory P Tochtrop
Aug 10, 2010·Current Opinion in Neurobiology·Christian BamannErnst Bamberg
Dec 27, 2011·Cell·Feng ZhangKarl Deisseroth
Jul 23, 2013·Biophysical Journal·Michaela MehlerClemens Glaubitz
Nov 26, 2013·Chemical Reviews·Rosana ÁlvarezÁngel R de Lera
Dec 25, 2013·Chemical Reviews·Oliver P ErnstHideki Kandori
Nov 22, 2014·Journal of the American Chemical Society·Jiafei MaoClemens Glaubitz
Apr 17, 2015·BioMed Research International·Elena DoldoAugusto Orlandi
Jul 29, 2015·Proceedings of the National Academy of Sciences of the United States of America·Johanna Becker-BaldusClemens Glaubitz

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Citations

Nov 23, 2019·Journal of the American Chemical Society·Jiafei MaoClemens Glaubitz

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