Synthesis of Deuterated-(C9)-11-cis-Retinal
Brown, Michael F.
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It has been shown that the dimerization of 2 vitamin A molecules with an Ethanolamine molecule leads to the formation of a molecule labeled as A2E. The latter is a phototoxic molecule and has been shown to be a major contributor to the detrimental eye condition, Age-related Macular Degeneration, AMD (1). Even though vitamin A dimerization is a contributor to this AMD condition, vitamin A is the very molecule that is necessary and key for human vision, hence it cannot be eliminated. It is been demonstrated experimentally that once carbon 20 of vitamin A was deuterated, the dimerization of vitamin A was reduced (1). Synthesis of retinal, one of many forms of vitamin A, has been well established (2, 3) and can be used to study vitamin A structure. Using similar synthetic routes and methods, we were able to introduce deuterium on carbon 9 of 11-cis-retinal.