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11-cis-retinal

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Organic Chemistry

Definition

11-cis-retinal is a light-sensitive molecule that plays a crucial role in the process of vision. It is a specific isomer of the retinal molecule, where the carbon-carbon double bond is in the cis configuration, meaning the two hydrogen atoms are on the same side of the double bond.

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5 Must Know Facts For Your Next Test

  1. 11-cis-retinal is the light-sensitive chromophore found in the photoreceptor cells of the eye, specifically the rod and cone cells.
  2. When 11-cis-retinal absorbs a photon of light, it undergoes a rapid isomerization to the all-trans configuration, initiating the visual transduction cascade.
  3. The isomerization of 11-cis-retinal to all-trans-retinal causes a conformational change in the photoreceptor protein, rhodopsin, which triggers a series of biochemical reactions that ultimately result in the generation of an electrical signal.
  4. The regeneration of 11-cis-retinal from all-trans-retinal is a critical step in the visual cycle, allowing the photoreceptors to regain their light sensitivity and continue the process of vision.
  5. The ability of 11-cis-retinal to undergo reversible isomerization in response to light is the fundamental basis for the chemistry of vision and the perception of color.

Review Questions

  • Explain the role of 11-cis-retinal in the process of vision and its relationship to the concept of conjugation.
    • 11-cis-retinal is the light-sensitive chromophore found in the photoreceptor cells of the eye. When 11-cis-retinal absorbs a photon of light, it undergoes a rapid isomerization to the all-trans configuration. This isomerization causes a conformational change in the photoreceptor protein, rhodopsin, which triggers a series of biochemical reactions that ultimately result in the generation of an electrical signal. The ability of 11-cis-retinal to undergo this reversible isomerization in response to light is the fundamental basis for the chemistry of vision and the perception of color. The conjugated system of double bonds in 11-cis-retinal allows for the efficient absorption and conversion of light energy, which is a key aspect of the conjugation discussed in the context of this chapter.
  • Describe how the isomerization of 11-cis-retinal to all-trans-retinal contributes to the chemistry of color vision.
    • The ability of 11-cis-retinal to undergo reversible isomerization in response to light is the fundamental basis for the chemistry of color vision. When 11-cis-retinal absorbs a photon of light, it isomerizes to the all-trans configuration, triggering a series of biochemical reactions that ultimately result in the generation of an electrical signal. This signal is then processed by the brain, allowing us to perceive color. The specific wavelength of light that is absorbed by 11-cis-retinal determines the type of photoreceptor (rod or cone) that is activated, and this in turn determines the color that is perceived. The conjugated system of double bonds in 11-cis-retinal plays a crucial role in its ability to efficiently absorb and convert light energy, which is a key aspect of the chemistry of color vision.
  • Analyze the importance of the reversible isomerization of 11-cis-retinal in the context of the visual cycle and the overall chemistry of vision.
    • The reversible isomerization of 11-cis-retinal is essential for the visual cycle and the overall chemistry of vision. When 11-cis-retinal absorbs a photon of light, it undergoes a rapid isomerization to the all-trans configuration, initiating the visual transduction cascade. This isomerization causes a conformational change in the photoreceptor protein, rhodopsin, which triggers a series of biochemical reactions that ultimately result in the generation of an electrical signal. The regeneration of 11-cis-retinal from all-trans-retinal is a critical step in the visual cycle, allowing the photoreceptors to regain their light sensitivity and continue the process of vision. Without this reversible isomerization, the photoreceptors would be unable to repeatedly respond to light, and the chemistry of vision would not be possible. The ability of 11-cis-retinal to undergo this reversible isomerization in response to light is the fundamental basis for the perception of color and the overall chemistry of vision.

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