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  • Title: 13-desmethyl rhodopsin and 13-desmethyl isorhodopsin: visual pigment analogues.
    Author: Nelson R, deRiel JK, Kropf A.
    Journal: Proc Natl Acad Sci U S A; 1970 Jun; 66(2):531-8. PubMed ID: 5271178.
    Abstract:
    The preparation and properties of three geometric isomers of 13-desmethyl retinal (13-dmr) are described. They are analogous to the all-trans, 11-cis, and 9-cis isomers of retinal since two of the cis isomers combine with cattle opsin to form pigments which are spectrally indistinguishable from rhodopsin and isorhodopsin and the all-trans isomer is unreactive.The pigment which resembles rhodopsin, 13-desmethyl (13-dm) rhodopsin, is formed at about one ninth the rate at which 11-cis retinal reacts with opsin at 20 degrees C. The reaction with 13-dmr does not go to completion; and 0.05 M hydroxylamine, to which rhodopsin is stable, decomposes 13-dm rhodopsin. Irradiation of 13-dm rhodopsin results in a cis --> trans isomerization of the chromophore; but the photosensitivity of 13-dm rhodopsin is only 40 per cent that of rhodopsin.13-dm isorhodopsin, the 13-desmethyl analogue of isorhodopsin, is formed at approximately the same specific rate as 13-dm rhodopsin. The reaction goes to completion and the pigment is not decomposed by 0.03 M hydroxylamine. 13-dm isorhodopsin can also be photolyzed to the all-trans chromophore plus opsin.
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