Journal of the American Chemical Society p. 2879 - 2882 (1983)
Update date:2022-08-17
Topics:
Rando, Robert R.
Chang, Andrew
The kinetics of the I2-catalyzed isomerization of the retinal isomers were studied.The all-trans isomer formed 13-cis-retinal rapidly with a rate constant 1.9E-4 s-1.The reverse reaction occurred with a rate constant of 4.5E-4 s-1.The 11-cis isomer was first converted to all-trans-retinal with a rate constant of 3.1E-4 s-1, although the 13-cis isomer was also rapidly formed.The 9-cis isomer was isomerized to the 9-cis, 13-cis isomer before the other isomers were generated and the 13-cis isomer was converted to its all-trans congener prior to the formation of the other isomers.Similar results appear to occur when other methods of catalysis are used.This isomerization about the C13-C14 double bond appears to be kinetically favored event, eliminating the possibility that 11-cis might be a kinetic product formed from the all-trans isomer.At equilibrium, only 0.1percent of 11-cis-retinal is found.Equilibration of all-trans-retinol palmitate also generated very little of the 11-cis-isomer (= 0.2percent) 11-cis-retinol palmitate at equilibrium.The implications of these results for an 11-cis-retinal regeneration mechanism in the eye are discussed.
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