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Synthesis and Properties of Bacteriorhodopsin Analogs Containing Electron-Density Labels in the Chromophore Moiety

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Abstract

A method for synthesis of retinal analogs labeled with electron-density groups is suggested. The interaction of these polyene compounds with bacterioopsin in apomembrane of Halobacterium salinarum was tested. A retinal analog containing a crown-ether receptor group is able to interact readily with bacterioopsin giving rise to rapid formation of a pigment with absorption maximum at 460 nm. This pigment is capable of undergoing cyclic photoconversion. The crown-bacteriorhodopsin photocycle is extremely slow and its quantum efficiency is very low (∼3% of that in native bacteriorhodopsin). This photocycle includes an M-like intermediate with a differential absorption maximum at 380 nm. A retinal analog in which the β-ionone ring is replaced by ferrocene moiety forms a stable chromoprotein with the main absorption band at 483 nm and a shoulder near 590-610 nm.

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Authors and Affiliations

  1. Lomonosov State Academy of Fine Chemical Technology, pr. Vernadskogo 86, Moscow, 117571, Russia

    E. V. Mironova, A. Yu. Lukin, S. V. Shevyakov, S. G. Alexeeva, V. I. Shvets & A. A. Khodonov

  2. Emanuel Institute for Biochemical Physics, Russian Academy of Sciences, ul. Kosygina 4, Moscow, 117977, Russia

    O. V. Demina

  3. Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, Moscow, 119899, Russia

    L. V. Khitrina

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  1. E. V. Mironova
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  2. A. Yu. Lukin
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  3. S. V. Shevyakov
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  4. S. G. Alexeeva
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  8. L. V. Khitrina
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Mironova, E.V., Lukin, A.Y., Shevyakov, S.V. et al. Synthesis and Properties of Bacteriorhodopsin Analogs Containing Electron-Density Labels in the Chromophore Moiety. Biochemistry (Moscow) 66, 1323–1333 (2001). https://doi.org/10.1023/A:1013147722255

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