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J. Biol. Chem., Vol. 275, Issue 36, 28128-28138, September 8, 2000
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From the Departments of Understanding of the stereospecificity of
enzymatic reactions that regenerate the universal chromophore required
to sustain vision in vertebrates, 11-cis-retinal, is needed
for an accurate molecular model of retinoid transformations. In rod
outer segments (ROS), the redox reaction involves
all-trans-retinal and pro-S-NADPH that results
in the production of pro-R-all-trans-retinol. A
recently identified all-trans-retinol dehydrogenase
(photoreceptor retinol dehydrogenase) displays identical
stereospecificity to that of the ROS enzyme(s). This result is unusual,
because photoreceptor retinol dehydrogenase is a member of a short
chain alcohol dehydrogenase family, which is often
pro-S-specific toward their hydrophobic alcohol substrates.
The second redox reaction occurring in retinal pigment epithelium,
oxidation of 11-cis-retinol, which is largely catalyzed by
abundantly expressed 11-cis-retinol dehydrogenase, is
pro-S-specific to both 11-cis-retinol and NADH.
However, there is notable presence of pro-R-specific
activities. Therefore, multiple retinol dehydrogenases are involved in
regeneration of 11-cis-retinal. Finally, the cellular
retinaldehyde-binding protein-induced isomerization of
all-trans-retinol to 11-cis-retinol proceeds
with inversion of configuration at the C15 carbon of
retinol. Together, these results provide important additions to our
understanding of retinoid transformations in the eye and a prelude for
in vivo studies that ultimately may result in efficient
pharmacological intervention to restore and prevent deterioration of
vision in several inherited eye diseases.
Stereoisomeric Specificity of the Retinoid Cycle in the
Vertebrate Retina*
,§,,, and§¶
Ophthalmology,
§ Chemistry, and ¶ Pharmacology, University of
Washington, Seattle, Washington 98195
*
This work was supported by a National Institutes of Health
Vision Training Grant (to J. K. M.), National Institutes of
Health Grant EY08061, an unrestricted grant from Research to Prevent Blindness, Inc. (to R. P. B. and the Department of
Ophthalmology at the University of Washington), a grant from Ruth and
Milton Steinbach Fund, and funds from the E. K. Bishop Foundation.The costs of publication of this
article were defrayed in part by the
payment of page charges. The article
must therefore be hereby marked
"advertisement" in
accordance with 18 U.S.C. Section
1734 solely to indicate this fact.
To whom correspondence should be addressed: University of
Washington, Dept. of Ophthalmology, Box 356485, Seattle, WA 98195-6485. Tel.: 206-543-9074; Fax: 206-221-6784; E-mail:
palczews@u.washington.edu.
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