Synthesis of 9-CD3-9-cis-retinal cofactor of isorhodopsin

Synthesis of 9-CD₃-9-cis-retinal cofactor of isorhodopsin

Research output: Contribution to journal › Article › peer-review

Laboratory of Biomolecular NMR

DOI

https://doi.org/10.1016/j.tetlet.2018.11.034
Final published version

Mozhgan Navidi
Shreya Yadav
Andrey V. Struts
Michael F. Brown
Nasri Nesnas

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.

Original language	English
Pages (from-to)	4521-4524
Number of pages	4
Journal	Tetrahedron Letters
Volume	59
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2018.11.034
State	Published - 19 Dec 2018

Scopus subject areas

Drug Discovery
Biochemistry
Organic Chemistry

Research areas

9-CD-9-cis-retinal, Isorhodopsin, Labeled retinal, Retinoids, Rhodopsin, LOCATION, CHROMOPHORE, ISOMERIZATION, NEUTRON-DIFFRACTION, EFFICIENT SYNTHESIS, 9-CD3-9-cis-retinal, RHODOPSIN, DYNAMICS, H-2 NMR, STEREOSELECTIVE-SYNTHESIS, VISUAL PIGMENT

ID: 36383372