71423-69-3Relevant articles and documents
Catalytic synthesis of 9-cis-retinoids: Mechanistic insights
Kahremany, Shirin,Kubas, Adam,Tochtrop, Gregory P.,Palczewski, Krzysztof
, p. 10581 - 10595 (2019/07/22)
The regioselective Z-isomerization of thermodynamically stable all-trans retinoids remains challenging, and ultimately limits the availability of much needed therapeutics for the treatment of human diseases. We present here a novel, straightforward approach for the catalytic Z-isomerization of retinoids using conventional heat treatment or microwave irradiation. A screen of 20 transition metal-based catalysts identified an optimal approach for the regioselective production of Z-retinoids. The most effective catalytic system was comprised of a palladium complex with labile ligands. Several mechanistic studies, including isotopic H/D exchange and state-of-the-art quantum chemical calculations using coupled cluster methods indicate that the isomerization is initiated by catalyst dimerization followed by the formation of a cyclic, six-membered chloropalladate catalyst-substrate adduct, which eventually opens to produce the desired Z-isomer. The synthetic development described here, combined with thorough mechanistic analysis of the underlying chemistry, highlights the use of readily available transition metal-based catalysts in straightforward formats for gram-scale drug synthesis.
One step and convenient preparations of 4-hydroxyretinal and 4- oxoretinal
Hashimoto, Masaru,Fujimoto, Yukari
, p. 3793 - 3797 (2007/10/03)
Treatment of all-trans-retinal with one and two equivalents of NBS in a mixture of CH3CN-CH2Cl2-H2O provide 4-hydroxyretinal and 4-oxoretinal, respectively, in good yields.
Photoaffinity labeling studies of bacteriorhodopsin with [ 15-3H]-3-diazo-4-keto-all-trans-retinal
Boehm, Marcus F.,Gawinowicz, Mary Ann,Foucault, Alain,Derguini, Fadila,Nakanishi, Koji
, p. 7779 - 7782 (2007/10/02)
Photoaffinity mapping can be used to help clarify the tertiary structures of the retinal proteins bacteriorhodopsin (bR) and rhodopsin (Rh). An efficient photoaffinity labeled retinal analogue, [l5-3H]-all-trans-3-diazo-4-ketoretinal (specific