Conformational Analysis of the Rhodopsin Chromophore Using 6-s-cis-Fixed Bicyclic Retinal Analogs

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  • 二環性レチナールアナログを用いるウシロドプシン発色団のコンホメーションの解析
  • ニカンセイ レチナール アナログ オ モチイル ウシロドプシン ハッショクダン

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Abstract

In order to investigate the conformation around the cyclohexene ring in the rhodopsin chromophore, we synthesized the bicyclic retinal analogs 7, in which C8 and C18 positions in retinal are connected by the methylene chain, and their interaction with bovine opsin was investigated. the enol triflates 17 which were readily derived from the bicyclic ketones 11 prepared from 2,2-dimethylcyclohexanone 9 via Dieckmann condensation of the diesters 10, were treated with methyl E-3-trimethylstannyl-2-butenoate in the presence of palladium diacetate to afford the β-ionylideneacetate ester analogs 18. These compounds were converted to the corresponding retinal analogs 7 via the Witting salts 22 and pentaenyl esters 23 or nitrile 26. The binding experiments of the retinal analogs 7 with bovine opsin gave the new artificial pigments 8 and from the comparison of opsin shift values, it was substantiated that the torsional angle around the 6-7 single bond in the rhodopsin chromophore is very close to that of rhodopsin analog 8b having a seven membered ring.

Journal

  • VITAMINS

    VITAMINS 71 (9), 407-414, 1997

    THE VITAMIN SOCIETY OF JAPAN

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