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Why 11-cis-Retinal? Why Not 7-cis 9-cis or 13-cis-Retinal in the Eye?

机译：为什么11顺 - 视？为什么不7顺9-顺或13顺 - 视的眼睛？

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摘要

One of the basic and unresolved puzzles in the chemistry of vision concerns the natural selection of 11-cis-retinal as the light-sensing chromophore in visual pigments. A detailed computational examination of the structure, stability, energetics and spectroscopy of 7-cis, 9-cis, 11-cis and 13-cis-retinal isomers in vertebrate (bovine, monkey) and invertebrate (squid) visual pigments is carried out using hybrid quantum mechanics/molecular mechanics (QM/MM) method. It is shown that the electrostatic interaction between retinal and opsin dominates the natural selection of 11-cis-retinal over other cis-isomers in the dark-state. In all the pigments, 9-cis-retinal is found to be only slightly higher in energy than 11-cis-retinal, which provides strong evidence for the presence of 9-cis-rhodopsin in nature. 7-cis-retinal is suggested to be an “upside-down” version of 11-trans-isomer because structural rearrangements observed for 7-cis-squid rhodopsin is found to be very similar to that of squid bathorhodopsin. The progressive red shift in the calculated absorption wavelength (λmax) of 7-cis- (431 nm), 9-cis- (456 nm), 11-cis- (490 nm) and 13-cis-retinal isomers (508 nm) are attributed to the decrease in bond length alternation of the retinal.

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    Sivakumar Sekharan; Keiji Morokuma;

  • 作者单位
  • 年(卷),期 -1(133),47
  • 年度 -1
  • 页码 19052–19055
  • 总页数 13
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