Reconstitution of gloeobacter rhodopsin with echinenone: Role of the 4-Keto group

Biochemistry

Volumn 49, Issue 45, 2010, Pages 9792-9799

  Balashov, Sergei P ^a   Imasheva, Eleonora S ^a   Choi, Ah Reum ^b   Jung, Kwang Hwan ^b   Liaaen Jensen, Synnve ^c   Lanyi, Janos K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Sogang University   (South Korea)

^c NORWEGIAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Norway)

Author keywords

[No Author keywords available]

Indexed keywords

CONJUGATED CHAIN; KETO DERIVATIVES; KETO GROUPS; LIGHT-HARVESTING ANTENNAS; PROTON PUMP; TWISTED CONFORMATION; XANTHORHODOPSIN;

ANTENNAS; BINDING SITES; CHROMOPHORES; CRYSTAL STRUCTURE; ENERGY HARVESTING; ENERGY TRANSFER; ESCHERICHIA COLI; OPHTHALMOLOGY; PIGMENTS; PUMPS; SUGARS;

BINDING ENERGY;

BACTERIAL PROTEIN; BETA CAROTENE; CAROTENOID; ECHINENONE; GLOEOBACTER RHODOPSIN; HYDROXYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CRYSTAL STRUCTURE; ENERGY TRANSFER; ENZYME RECONSTITUTION; ESCHERICHIA COLI; LIGHT HARVESTING SYSTEM; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN EXPRESSION;

BETA CAROTENE; CAROTENOIDS; CIRCULAR DICHROISM; ESCHERICHIA COLI; GLYCOSIDES; MODELS, MOLECULAR; RHODOPSIN; RHODOPSINS, MICROBIAL; SPECTROPHOTOMETRY; XANTHINE;

ESCHERICHIA COLI; GLOEOBACTER;

EID: 78149424829     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi1014166     Document Type: Article

References (45)

1. Lanyi, J. K. (2006) Proton transfers in the bacteriorhodopsin photocycle Biochim. Biophys. Acta 1757, 1012-1018
2. Oesterhelt, D. and Stoeckenius, W. (1973) Functions of a new photoreceptor membrane Proc. Natl. Acad. Sci. U.S.A. 70, 2853-2857
3. Béjà, O., Aravind, L., Koonin, E. V., Suzuki, M. T., Hadd, A., Nguyen, L. P., Jovanovich, S. B., Gates, C. M., Feldman, R. A., Spudich, J. L., Spudich, E. N., and DeLong, E. F. (2000) Bacterial rhodopsin: Evidence for a new type of phototrophy in the sea Science 289, 1902-1906
4. Drachev, L. A., Frolov, V. N., Kaulen, A. D., Liberman, E. A., Ostroumov, S. A., Plakunova, G. V., Semenov, A. Y., and Skulachev, V. P. (1976) Reconstitution of biological molecular generators of electric current. Bacteriorhodopsin J. Biol. Chem. 251, 7059-7065
5. Michel, H. and Oesterhelt, D. (1980) Light-induced changes of the pH gradient and the membrane potential in Halobacterium halobium FEBS Lett. 65, 175-178
6. Sineshchekov, O. A. and Spudich, J. L. (2004) Light-induced intramolecular charge movements in microbial rhodopsins in intact E. coli cells Photochem. Photobiol. Sci. 3, 548-554
7. Wang, W. W., Sineshchekov, O. A., Spudich, E. N., and Spudich, J. L. (2003) Spectroscopic and photochemical characterization of a deep ocean proteorhodopsin J. Biol. Chem. 278, 33985-33991
8. Béjà, O., Spudich, E. N., Spudich, J. L., Leclerc, M., and DeLong, E. F. (2001) Proteorhodopsin phototrophy in the ocean Nature 411, 786-789
9. Sabehi, G., Massana, R., Bielawski, J. P., Rosenberg, M., Delong, E. F., and Béjà, O. (2003) Novel Proteorhodopsin variants from the Mediterranean and Red Seas Environ. Microbiol. 5, 842-849
10. Venter, J. C., Remington, K., Heidelberg, J. F., Halpern, A. L., Rusch, D., Eisen, J. A., Wu, D., Paulsen, I., Nelson, K. E., Nelson, W., Fouts, D. E., Levy, S., Knap, A. H., Lomas, M. W., Nealson, K., White, O., Peterson, J., Hoffman, J., Parsons, R., Baden-Tillson, H., Pfannkoch, C., Rogers, Y.-H., and Smith, H. O. (2004) Environmental genome shotgun sequencing of the Sargasso Sea Science 304, 66-74
11. Spudich, J. L. and Jung, K.-H. (2005) Microbial Rhodopsins: Phylogenetic and Functional Diversity. In Handbook of photosensory receptors (Briggs, W. R. and Spudich, J. L., Eds.) pp 1 - 23, Wiley-VCH, Darmstadt, Germany.
12. Fuhrman, J. A., Schwalbach, M. S., and Stingl, U. (2008) Proteorhodopsins: An array of physiological roles? Nat. Rev. Microbiol. 6, 488-494
13. Balashov, S. P., Imasheva, E. S., Boichenko, V. A., Antón, J., Wang, J. M., and Lanyi, J. K. (2005) Xanthorhodopsin: A proton pump with a light-harvesting carotenoid antenna Science 309, 2061-2064
14. 40-carotenoid acyl glycoside as principal carotenoid in Salinibacter ruber, an extremely halophilic eubacterium J. Nat. Prod. 65, 1340-1343
15. Balashov, S. P., Imasheva, E. S., Wang, J. M., and Lanyi, J. K. (2008) Excitation energy-transfer and the relative orientation of retinal and carotenoid in xanthorhodopsin Biophys. J. 95, 2402-2414
16. Boichenko, V. A., Wang, J. M., Antón, J., Lanyi, J. K., and Balashov, S. P. (2006) Functions of carotenoids in xanthorhodopsin and archaerhodopsin, from action spectra of photoinhibition of cell respiration Biochim. Biophys. Acta 1757, 1649-1656
17. Polívka, T., Balashov, S. P., Chábera, P., Imasheva, E. S., Yartsev, A., Sundström, V., and Lanyi, J. K. (2009) Femtosecond carotenoid to retinal energy transfer in xanthorhodopsin Biophys. J. 96, 2268-2277
18. Birge, R. R. (1990) Nature of the primary photochemical events in rhodopsin and bacteriorhodopsin Biochim. Biophys. Acta 1016, 293-327
19. Fujimoto, K. J. and Hayashi, S. (2009) Electronic Coulombic coupling of excitation-energy transfer in xanthorhodopsin J. Am. Chem. Soc. 131, 14152-14153
20. Luecke, H., Schobert, B., Stagno, J., Imasheva, E. S., Wang, J. M., Balashov, S. P., and Lanyi, J. K. (2008) Crystallographic structure of xanthorhodopsin, the light-driven proton pump with a dual chromophore Proc. Natl. Acad. Sci. U.S.A. 105, 16561-16565
21. Balashov, S. P., Imasheva, E. S., and Lanyi, J. K. (2006) Induced chirality of the light-harvesting carotenoid salinixanthin and its interaction with the retinal of xanthorhodopsin Biochemistry 45, 10998-11004
22. Smolensky, E. and Sheves, M. (2009) Retinal-salinixanthin interactions in xanthorodopsin: A circular dichroism (CD) spectroscopy study with artificial pigments Biochemistry 48, 8179-8188
23. Imasheva, E. S., Balashov, S. P., Choi, A. R., Jung, K.-H., and Lanyi, J. K. (2009) Reconstitution of Gloeobacter violaceus rhodopsin with a light-harvesting carotenoid antenna Biochemistry 48, 10948-10955
24. Miranda, M. R. M., Choi, A. R., Shi, L., Bezerra, A. G., Jung, K.-H., and Brown, L. S. (2009) The photocycle and proton translocation pathway in a cyanobacterial ion-pumping rhodopsin Biophys. J. 96, 1471-1481
25. Takaichi, S. and Mochimaru, M. (2007) Carotenoids and carotenogenesis in cyanobacteria: Unique ketocarotenoids and carotenoid glycosides Cell. Mol. Life Sci. 64, 2607-2619
26. Britton, G., Liaaen-Jensen, S., and Pfander, H., Eds. (2004) Carotenoids Handbook, Birkhauser Verlag, Basel, Switzerland.
27. Christensen, R. L. and Kohler, B. E. (1973) Low resolution optical spectroscopy of retinyl polyenes: Low lying electronic levels and spectral broadness Photochem. Photobiol. 1973, 293-301
28. Britton, G. (1995) UV/Visible Spectroscopy. In Carotenoids Volume 1B: Spectroscopy (Britton, G., Liaaen-Jensen, S., and Pfander, H., Eds.) pp 13 - 62, Birkhauser Verlag, Basel, Switzerland.
29. Kouyama, T., Kinosita, K., and Ikegami, A. (1985) Excited-state dynamics of bacteriorhodopsin Biophys. J. 47, 43-54
30. Balashov, S. P., Litvin, F. F., and Sineshchekov, V. A. (1988) Photochemical processes of light energy transformation in bacteriorhodopsin. In Physicochemical Biology Reviews (Skulachev, V. P., Ed.) pp 1 - 61, Harwood Academic Publishers GmbH, Basingstoke, U.K.
31. 1 states J. Phys. Chem. B 107, 5995-6002
32. Holt, N. E., Kennis, J. T. M., and Fleming, G. R. (2004) Femtosecond fluorescence upconversion studies of light harvesting by β-carotene in oxygenic photosynthetic core proteins J. Phys. Chem. B 108, 19029-19035
33. Polívka, T. and Frank, H. A. (2010) Molecular factors controlling photosynthetic light harvesting by carotenoids Acc. Chem. Res. 43, 1125-1134
34. Roszak, A. W., McKendrick, K., Gardiner, A. T., Mitchell, I. A., Isaacs, N. W., Cogdell, R. J., Hashimoto, H., and Frank, H. A. (2004) Protein regulation of carotenoid binding: Gatekeeper and locking amino acid residues in reaction centers of Rhodobacter sphaeroides Structure 12, 765-773
35. Kerfeld, C. A., Sawaya, M. R., Brahmandam, V., Cascio, D., Ho, K. K., Trevithick-Sutton, C. C., Krogmann, D. W., and Yeates, T. O. (2003) The crystal structure of a cyanobacterial water-soluble carotenoid binding protein Structure 11, 55-65
36. Punginelli, C., Wilson, A., Routaboul, J. M., and Kirilovsky, D. (2009) Influence of zeaxanthin and echinenone binding on the activity of the Orange Carotenoid Protein Biochim. Biophys. Acta 1787, 280-288
37. Polívka, T., Kerfeld, C. A., Pascher, T., and Sundström, V. (2005) Spectroscopic properties of the carotenoid 3?-hydroxyechinenone in the orange carotenoid protein from the cyanobacterium Arthrospira maxima Biochemistry 44, 3994-4003
38. Ke, B., Imsgard, F., Kjosen, H., and Liaaen-Jensen, S. (1970) Electronic spectra of carotenoids at 77 degrees K Biochim. Biophys. Acta 210, 139-152
39. Chabera, P., Fuciman, M., Hribek, P., and Polívka, T. (2009) Effect of carotenoid structure on excited-state dynamics of carbonyl carotenoids Phys. Chem. Chem. Phys. 11, 8795-8803
40. Hashimoto, H., Yoda, T., Kobayashi, T., and Young, A. J. (2002) Molecular structures of carotenoids as predicted by MNDO-AM1 molecular orbital calculations J. Mol. Struct. 604, 125-146
41. Sterling, C. (1964) Crystal-structure analysis of β-carotene Acta Crystallogr. 17, 1224-1228
42. Bart, J. C. and MacGillavry, C. H. (1968) The crystal and molecular structure of canthaxanthin Acta Crystallogr. B24, 1587-1606
43. Bartalucci, G., Coppin, J., Fisher, S., Hall, G., Helliwell, J. R., Helliwell, M., and Liaaen-Jensen, S. (2007) Unravelling the chemical basis of the bathochromic shift in the lobster carapace; new crystal structures of unbound astaxanthin, canthaxanthin and zeaxanthin Acta Crystallogr. B63, 328-337
44. Cianci, M., Rizkallah, P. J., Olczak, A., Raftery, J., Chayen, N. E., Zagalsky, P. F., and Helliwell, J. R. (2002) The molecular basis of the coloration mechanism in lobster shell: β-Crustacyanin at 3.2-Å resolution Proc. Natl. Acad. Sci. U.S.A. 99, 9795-9800
45. Pal, D. and Chakrabarti, P. (2001) Non-hydrogen bond interactions involving the methionine sulfur atom J. Biomol. Struct. Dyn. 19, 115-128