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

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

Research output: Contribution to journalArticle

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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.

Original languageEnglish (US)
Pages (from-to)4521-4524
Number of pages4
JournalTetrahedron Letters
Volume59
Issue number51
DOIs
Publication statusPublished - Dec 19 2018

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Keywords

  • 9-CD-9-cis-retinal
  • Isorhodopsin
  • Labeled retinal
  • Retinoids
  • Rhodopsin

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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