Steric hindrance between chromophore substituents as the driving force of rhodopsin photoisomerization: 10-methyl-13-demethyl retinal containing rhodopsin.

Abstract:

:A visual chromophore analogue, 10-methyl-13-demethyl (dm) retinal, was synthesized and reconstituted with bleached bovine rhodopsin to form a visual pigment derivative with absorbance maximum at 505 nm. The investigations with this new compound were stimulated from recent results using 13-dm retinal as a chromophore that revealed a remarkable loss in quantum efficiency (phi of 13-dm retinal-containing rhodopsin: 0.30, Ternieden and Gärtner, J. Photochem. Photobiol. B Biol, 33, 83-86, 1996). The quantum efficiency of the new pigment was determined as 0.59 by quantitative bleaching using reconstituted rhodopsin as a reference. The very similar quantum efficiencies of rhodopsin and the new pigment give experimental support for the recently presented hypothesis that a steric hindrance between the substituents at positions 10 and 13 in 11-cis-retinal is elevated during the photoisomerization and thus facilitates the rapid photoisomerization of the visual chromophore (Peteanu et al., Proc. Natl. Acad. Sci. USA 90, 11762-11766, 1993). Such steric hindrance is removed from the molecule by the elimination of the methyl group from position 13 and can be re-established via a rearrangement of the substitution pattern by introducing a methyl group at position 10 of 13-dm retinal.

journal_name

Photochem Photobiol

authors

Koch D,Gärtner W

doi

10.1111/j.1751-1097.1997.tb01896.x

subject

Has Abstract

pub_date

1997-01-01 00:00:00

pages

181-6

issue

1

eissn

0031-8655

issn

1751-1097

journal_volume

65

pub_type

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