3 years ago

Synthesis of Isotopically Labelled All-Trans Retinals for DNP-Enhanced Solid State NMR Studies of Retinylidene Proteins

Johanna Becker-Baldus, Michaela Mehler, Richard C.D. Brown, Lynda J. Brown, Alexander J. Leeder, Clemens Glaubitz
Three all-trans retinals containing multiple 13C labels have been synthesised to enable DNP enhanced solid-state MAS NMR studies of novel microbial retinylidene membrane proteins including proteorhodpsin and channelrhodopsin. The synthetic aproaches allowed specific introduction of 13C 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. [10-18-13C9]-All-trans-retinal (1b), [12,15-13C2]-all-trans-retinal (1c) and [14,15-13C2]-all-trans-retinal (1d) were synthesised in in twelve, eight and seven linear steps from ethyl 2-oxocyclohexanecarboxylate (5) or β-ionone (4) respectively.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/jlcr.3576

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