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AZIDOTETRAFLUOROPHENYL RETINAL ANALOGUE: SYNTHESIS AND BACTERIORHODOPSIN PIGMENT FORMATION
Author(s) -
Beischel Charles J.,
Knapp Daniel R.,
Govindjee Rajni,
Ebrey Thomas G.,
Crouch Rosalie K.
Publication year - 1994
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.1751-1097.1994.tb03944.x
Subject(s) - chromophore , bacteriorhodopsin , chemistry , polyene , retinal , photochemistry , reagent , stereochemistry , organic chemistry , biochemistry , membrane
—The retinal derivative, all‐truns‐9–(4‐azido‐2,3,5,6‐tetrafluorophenyl)‐3,7‐dimethyl‐2,4,6,8‐nonatetraenal, was synthesized by two routes as a potential photoactivatable cross‐linking agent for studies in bacteriorhodopsin (BR) of the chromophore interaction with its apoprotein. The retinal analogue formed a stable, moderately functional BR pigment confirming that the ring cavity of the retinal binding site has a significant tolerance for derivatization on that portion of the molecule. Attempts to cross‐link the azido chromophore to the protein by photoactivation were unsuccessful. The electron delocalization effect of the conjugated polyene side chain of the retinal appears to interfere with the formation or reactivity of the nitrene intermediate to the extent that photoactivated cross‐linking is not achieved. These results demonstrate a limitation to the use of fluorinated aryl azides as photoaffinity reagents.