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A POSSIBLE MECHANISM FOR THE ROLE OF N ‐RETINYLIDENE PHOSPHATIDYL ETHANOLAMINE IN THE REGENERATION OF RHODOPSIN
Author(s) -
Rabinovitch B.
Publication year - 1979
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1979.tb07091.x
Subject(s) - chemistry , photoisomerization , polyene , protonation , schiff base , moiety , rhodopsin , photochemistry , isomerization , excited state , stereochemistry , ion , retinal , organic chemistry , biochemistry , physics , nuclear physics , catalysis
— A series of molecular orbital calculations on a model Schiff base comparable to protonated N ‐retinylidene phosphatidyl ethanolamine isomers has been made. The effect of the charged oxygen atoms of the phosphate moiety on the distribution of positive charge along the polyene chain of these isomers has been calculated. The stabilizing coulombic energy of interaction of these opposite charges and the possibility of free rotation around carbonxarbon double bonds in the electronically excited state has led to the conclusion that an 11‐ cis Schiff base isomer is the most probable product of the photoisomerization of an all‐trans Schiff base. The formation of a stable unprotonated all‐trans Schiff base in aqueous detergent dispersion and its subsequent conversion to the protonated form, both with absorption spectra in conformity with the literature, is demonstrated.