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. 2018 Dec 19;59(51):4521-4524.
doi: 10.1016/j.tetlet.2018.11.034. Epub 2018 Nov 10.

Synthesis of 9-CD3-9- cis-Retinal Cofactor of Isorhodopsin

Mozhgan Navidi  1 , Shreya Yadav  1 , Andrey V Struts  2 , Michael F Brown  2 , Nasri Nesnas  1
Affiliations

Synthesis of 9-CD3-9- cis-Retinal Cofactor of Isorhodopsin

Mozhgan Navidi et al. Tetrahedron Lett. .

Abstract

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 their corresponding DIBAL reductions. A final oxidation of the allylic alcohol of the retinol leads to the target compound. This deuterium labeled retinoid is an important cofactor for studying protein-retinoid interactions in isorhodopsin.

Keywords: 9-CD3-9-cis-retinal; Retinoids; isorhodopsin; labeled retinal; rhodopsin.

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Figures

Figure 1.
Figure 1.
Structures of 11-cis-retinal and 9-cis-retinal.
Figure 2.
Figure 2.
Examples of reported retinoids.
Figure 3.
Figure 3.
Carbanion formed in Horner–Wadsworth–Emmons reaction.
Figure 4.
Figure 4.
Electronic UV spectra of synthesized 9-CD3-9-cis-retinal (blue), commercial 9-cis-retinal (red), and commercial alltrans-retinal (green). Solutions contained 1.7 × 10−3 M retinoids in n-hexane at room temperature. The absorption maximum (λmax) obtained for 9-CD3-9-cis-retinal and 9-cis-retinal was 366 nm; while for all-trans-retinal λmax it was at 370 nm.
Scheme 1.
Scheme 1.
Synthesis of the Z aldehyde 11.
Scheme 2.
Scheme 2.
Synthesis of 9-CD3-9Z-retinal.
See this image and copyright information in PMC

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