2001年10月
Retinoids and related compounds. Part 26. Synthesis of (11 Z)-8,18-propano- and methano-retinals and conformational study of the rhodopsin chromophore
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
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- 巻
- 号
- 19
- 開始ページ
- 2430
- 終了ページ
- 2439
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1039/b104394n
- 出版者・発行元
- ROYAL SOC CHEMISTRY
In order to clarify, the conformation of the chromophore in rhodopsin, especially the effect of the torsional angle around the C6-C7 single bond on the CD spectrum, 8,18-propano- and methano-retinal 4 and 5 were prepared via the palladium-catalyzed coupling reaction of vinyl triflates derived from bicyclic ketones 10 and 17 with methyl (E)-3-(trimethylstannyl)but-2-enoate. In a binding experiment with bovine opsin, retinal analogs 4 and 5 afforded the new rhodopsin analogs. Although the opsin shifts of these pigments ware similar to that of the native rhodopsin, CD spectra exhibited the characteristic feature owing to, the locked structures of retinal analogs. This fact strongly indicates that the CD spectra were significantly influenced by the torsional angles around the 6-7 and 8-9 single bonds of the chromophore in the protein.
- リンク情報
- ID情報
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- DOI : 10.1039/b104394n
- ISSN : 1472-7781
- J-Global ID : 200902171883934173
- Web of Science ID : WOS:000171794000015