retinal methylimine Schiff base | 51424-44-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: retinal methylimine Schiff base
• 英文别名: Isorhodopsin；all-trans-retinal-methylimine；all-trans-Retinal-methylimin；all-trans-Methylretinal-schiffbase；Retinyliden-methylamin；(2E,4E,6E,8E)-N,3,7-trimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-imine
• CAS: 51424-44-3
• 化学式: C₂₁H₃₁N
• 分子量: 297.484
• InChiKey: ZIBZWVGZUUDYER-FKGJSDGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  retinal methylimine Schiff base 在 碘甲烷 作用下， 生成 [3,7-dimethyl-9t-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2t,4t,6t,8-tetraenylidene]-dimethyl-ammonium; iodide
  参考文献：
  名称：

  Pitt et al., Biochemical Journal, 1955, vol. 59, p. 122,124

  摘要：

  DOI：
• 作为产物：
  描述：

  视黄醛 在 甲胺 、 Petroleum ether 作用下， 生成 retinal methylimine Schiff base
  参考文献：
  名称：

  Pitt et al., Biochemical Journal, 1955, vol. 59, p. 122,124

  摘要：

  DOI：

文献信息

• High-resolution carbon-13 NMR of retinal derivatives in the solid state
  作者：G. S. Harbison、P. P. J. Mulder、H. Pardoen、J. Lugtenburg、J. Herzfeld、R. G. Griffin

  DOI：10.1021/ja00303a001

  日期：1985.8

  tran~duction.~~~ However, in neither case are the spectroscopic properties of the intact protein similar to those of the free aldehydes, or of simple model compounds derived from it. Clearly, therefore, the conformational and electronic properties of the chromophores are strongly modulated by the approtein, and an understanding of the differences between bacteriorhodospin and rhodospin on the one hand, and retinal

  大量结晶性视黄醛衍生物的 I3C 核磁共振谱已通过使用交叉极化和魔角样品旋转获得。大多数衍生物产生的光谱具有窄线（宽度约 20 Hz），可以通过它们的 13C-'H 偶极耦合、它们的化学位移张量、与溶液光谱的比较或特定标记来分配。光谱中旋转边带强度的测量允许计算化学屏蔽张量，这些数据使我们能够更详细地分析这些化合物的各向同性位移的变化。我们表明，张量表现出奇/偶效应，这是由多烯链一侧的空间拥挤引起的，*-电子扰动主要影响张量的面内元素，相反，由于顺反异构化产生的强空间相互作用会影响面外元素。最后，我们观察到关于 6-7 键异构化的 C-5 位置的低场位移，因此从观察到的位移推断视黄醛衍生物在溶液中为 25-30% 6-s-反式。多烯醛全反式视黄醛及其几何异构体在视紫红质和其他视觉以及细菌视紫红质和其他光驱动膜泵中起着核心作用^。^^^ 在这两种类型的系统中，光子诱导异构化是初始事件光转导。~~~
• Spontaneous Emission Study of the Femtosecond Isomerization Dynamics of Rhodopsin
  作者：Gerd. G. Kochendoerfer、Richard A. Mathies

  DOI：10.1021/jp960509+

  日期：1996.1.1

  The spontaneous emission spectra and yields of the visual pigment rhodopsin and its 9-cis retinal analog isorhodopsin have been measured following excitation at 472.7, 514.5, and 568.2 nm. The fluorescence quantum yields are (0.9 +/- 0.3) x 10(-5) for rhodopsin and (1.8 +/- 0.7) x 10(-5) for isorhodopsin. By use of a Strickler-Berg analysis, these quantum yields correspond to excited electronic state lifetimes of 50 and 100 fs for rhodopsin and isorhodopsin, respectively. The fluorescence spectra also undergo a blue-shift of similar to 1800 cm(-1) upon shifting the excitation wavelength from 568.2 to 472.7 nm. This is consistent with the idea that the emission arises from unrelaxed, nonstationary vibrational states. For rhodopsins, there is a correlation among these rapid initial nuclear dynamics out of the Franck-Condon region, the rapid photoisomerization rates, and the high isomerization quantum yields. These results support a new mechanism for the isomerization reaction dynamics in visual pigments where the reaction efficiency is mechanistically linked to the reaction rate through a dynamic Landau-Zener tunneling process.