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Z-isomerization of retinoids through combination of monochromatic photoisomerization and metal catalysis.


ABSTRACT: Catalytic Z-isomerization of retinoids to their thermodynamically less stable Z-isomer remains a challenge. In this report, we present a photochemical approach for the catalytic Z-isomerization of retinoids using monochromatic wavelength UV irradiation treatment. We have developed a straightforward approach for the synthesis of Z-retinoids in high yield, overcoming common obstacles normally associated with their synthesis. Calculations based on density functional theory (DFT) have allowed us to correlate the experimentally observed Z-isomer distribution of retinoids with the energies of chemically important intermediates, which include ground- and excited-state potential energy surfaces. We also demonstrate the application of the current method by synthesizing gram-scale quantities of 9-cis-retinyl acetate 9Z-a. Operational simplicity and gram-scale ability make this chemistry a very practical solution to the problem of Z-isomer retinoid synthesis.

SUBMITTER: Kahremany S 

PROVIDER: S-EPMC6739180 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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Z-isomerization of retinoids through combination of monochromatic photoisomerization and metal catalysis.

Kahremany Shirin S   Sander Christopher Lane CL   Tochtrop Gregory P GP   Kubas Adam A   Palczewski Krzysztof K  

Organic & biomolecular chemistry 20190828 35


Catalytic Z-isomerization of retinoids to their thermodynamically less stable Z-isomer remains a challenge. In this report, we present a photochemical approach for the catalytic Z-isomerization of retinoids using monochromatic wavelength UV irradiation treatment. We have developed a straightforward approach for the synthesis of Z-retinoids in high yield, overcoming common obstacles normally associated with their synthesis. Calculations based on density functional theory (DFT) have allowed us to  ...[more]

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