レチノイド異性体の立体選択的合成とタンパク質機能解明への応用

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A stereoselective synthesis of retinoid isomers, which are signal molecules of retinoid proteins such as rhodopsin, retinochrome, retinoic acid receptor, retinoid x receptor, and so forth, was devel oped from the β-ionone-tricarbonyliron complex 1. Treatment of the complex 1, prepared from the reaction of β-ionone and dodecacarbonyltriiron, with the lithium salt of acetonitrile afforded the nitrile 2, on the contrary, the reaction of the complex 1 with the lithium enolate of ethyl acetate and subsequent dehydration gave the ethyl 9Z-β- ionylideneacetate 9 predominantly. These compounds (2 and 9) were converted to the corresponding all-E- and 9Z- retinoic acids (7 and 16) via β-ionylideneacetaldehydes (3 and 12), respectively. The Peterson reaction of the aidehyde complex 3 with ethyl trimethylsilylacetate provided the 11Z-isomer 18 preferentially accompanied by the 11E-isomer 17. The ester 18 was transformed into the 11Z- retinal 30 in good yield without isomerization of double bonds. In order to investigate the interaction between the 9-substituents of retinal and apoprotein of rhodop sin, various 9-substituted 11Z-retinals 42 were synthesized by applying our developed method. The binding experiments of retinal analogs 42 with bovine opsin gave the new artificial pigments except for phenyl, (1-naphthyl)methyl, and tertiary butyl substituents in the alanogs 42, and the conforma tional analysis of chromophore in these pigments was also discussed.
日本ビタミン学会の論文
2000-03-25

レチノイド異性体の立体選択的合成とタンパク質機能解明への応用

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