Two stereoisomers of spheroidene in the Rhodobacter sphaeroides R26 reaction center: A DFT analysis of resonance raman spectra

Biophysical Journal

Volumn 93, Issue 3, 2007, Pages 981-991

  Wirtz, A C ^a   Van Hemert, M C ^b   Lugtenburg, J ^b   Frank, H A ^c   Groenen, E J J ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b LEIDEN UNIVERSITY   (Netherlands)

^c UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CAROTENOID; SPHEROIDENE; UNCLASSIFIED DRUG;

ARTICLE; CIS ISOMER; DENSITY FUNCTIONAL THEORY; ISOTOPE LABELING; ISOTOPOMER; LIGHT HARVESTING SYSTEM; NONHUMAN; PHOTOSYNTHESIS; RAMAN SPECTROMETRY; RHODOBACTER SPHAEROIDES; STEREOISOMERISM; THEORETICAL MODEL;

RHODOBACTER SPHAEROIDES;

EID: 34547700384     PISSN: 00063495     EISSN: None     Source Type: Journal    
DOI: 10.1529/biophysj.106.103473     Document Type: Article

References (34)

1. Cogdell, R. J., and H. A. Frank. 1987. How carotenoids function in photosynthetic bacteria. Biochim. Biophys. Acta. 895:63-79.
2. Koyama, Y. 1991. Structures and functions of carotenoids in photosynthetic systems. J. Photochem. Photobiol. B Biol. 9:265-280.
3. Cogdell, R. J., W. W. Parson, and M. A. Kerr. 1976. The type, amount, location, and energy transfer properties of the carotenoid in reaction centers from Rhodopseudomonas sphaeroides. Biochim. Biophys. Acta. 430:83-93.
4. Foote, C. S., Y. C. Chang, and R. W. Denny. 1970. Chemistry of singlet oxygen. X. Carotenoid quenching parallels biological protection. J. Am. Chem. Soc. 92:5216-5218.
5. Lutz, M., J. Kleo, and F. Reiss-Husson. 1976. Resonance Ramanscattering of bacteriochlorophyll, bacteriopheophytin and spheroidene in reaction centers of Rhodopseudomonas spheroides. Biochem. Biophys. Res. Commun. 69:711-717.
6. Pendon, Z. D., K. van der Hoef, J. Lugtenburg, and H. A. Frank. 2006. Triplet state spectra and dynamics of geometric isomers of carotenoids. Photosynth. Res. 88:51-61.
7. Lutz, M., I. Agalidis, G. Hervo, R. J. Cogdell, and F. Reiss-Husson. 1978. On the state of carotenoids bound to reaction centers of photosynthetic bacteria: a resonance Raman study. Biochim. Biophys. Acta. 503:287-303.
8. Agalidis, I., M. Lutz, and F. Reiss-Husson. 1980. Binding of carotenoids on reaction centers from Rhodopseudomonas sphaeroides R 26. Biochim. Biophys. Acta. 589:264-274.
9. Chadwick, B. W., and H. A. Frank. 1986. Electron-spin resonance studies of carotenoids incorporated into reaction centers of Rhodobacter sphaeroides R26.1. Biochim. Biophys. Acta. 851:257-266.
10. Frank, H. A., and C. A. Violette. 1989. Monomeric bacteriochlorophyll is required for the triplet energy transfer between the primary donor and the carotenoid in photosynthetic bacterial reaction centers. Biochim. Biophys. Acta. 976:222-232.
11. Roszak, A. W., K. McKendrick, A. T. Gardiner, I. A. Mitchell, N. W. Isaacs, R. J. Cogdell, H. Hashimoto, and H. A. Frank. 2004. Protein regulation of carotenoid binding: gatekeeper and locking amino acid residues in reaction centers of Rhodobacter sphaeroides. Structure. 12:765-773.
12. Lutz, M., W. Szponarski, G. Berger, B. Robert, and J. M. Neumann. 1987. The stereoisomerism of bacterial, reaction-center-bound carotenoids revisited - an electronic absorption, resonance Raman and H-1-NMR study. Biochim. Biophys. Acta. 894:423-433.
13. Koyama, Y., M. Kito, T. Takii, K. Saiki, K. Tsukida, and J. Yamashita. 1982. Configuration of the carotenoid in the reaction centers of photosynthetic bacteria - comparison of the resonance Raman spectrum of the reaction center of Rhodopseudomonas-sphaeroides g1c with those of cis-trans isomers of beta-carotene. Biochim. Biophys. Acta. 680:109-118.
14. Koyama, Y., T. Takii, K. Saiki, and K. Tsukida. 1983. Configuration of the carotenoid in the reaction centers of photosynthetic bacteria. 2. Comparison of the resonance Raman lines of the reaction centers with those of the 14 different cis-trans isomers of beta-carotene. Photobiochem. Photobiophys. 5:139-150.
15. de Groot, H. J. M., R. Gebhard, K. van der Hoef, A. J. Hoff, J. Lugtenburg, C. A. Violette, and H. A. Frank. 1992. C-13 magic angle spinning NMR evidence for a 15,15′-cis configuration of the spheroidene in the Rhodobacter-sphaeroides photosynthetic reaction center. Biochemistry. 31:12446-12450.
16. Bautista, J. A., V. Chynwat, A. Cua, F. J. Jansen, J. Lugtenburg, D. Gosztola, M. R. Wasielewski, and H. A. Frank. 1998. The spectroscopic and photochemical properties of locked-15,15′-cis-spheroidene in solution and incorporated into the reaction center of Rhodobacter sphaeroides R-26.1. Photosynth. Res. 55:49-65.
17. Arnoux, B., A. Ducruix, F. Reiss-Husson, M. Lutz, J. Norrise, M. Schiffer, and C. H. Chang. 1989. Structure of spheroidene in the photosynthetic reaction center from y Rhodobacter sphaeroides. FEBS Lett. 258:47-50.
18. Feher, G., J. P. Allen, M. Y. Okamura, and D. C. Rees. 1989. Structure and function of bacterial photosynthetic reaction centers. Nature. 339:111-116.
19. Ermler, U., G. Fritzsch, S. K. Buchanan, and H. Michel. 1994. Structure of the photosynthetic reaction center from Rhodobacter sphaeroides at 2.65-Å ngstrom resolution - cofactors and protein-cofactor interactions. Structure. 2:925-936.
20. McAuley, K. E., P. K. Fyfe, J. P. Ridge, R. J. Cogdell, N. W. Isaacs, and M. R. Jones. 2000. Ubiquinone binding, ubiquinone exclusion, and detailed cofactor conformation in a mutant bacterial reaction center. Biochemistry. 39:15032-15043.
21. Kok, P., J. Köhler, E. J. J. Groenen, R. Gebhard, K. van der Hoef, J. Lugtenburg, A. J. Hoff, R. Farhoosh, and H. A. Frank. 1994. Before a vibrational analysis of spheroidene - resonance Raman-spectroscopy of C-13-labeled spheroidenes in petroleum ether and in the Rhodobacter- sphaeroides reaction center. Biochim. Biophys. Acta. 1185:188-192.
22. Kok, P., J. Köhler, E. J. J. Groenen, R. Gebhard, K. van der Hoef, J. Lugtenburg, R. Farhoosh, and H. A. Frank. 1997. Resonance Raman spectroscopy of 2H-labeled spheroidenes in petroleum ether and in the Rhodobacter sphaeroides reaction centre. Spectr. Acta A Molec. Biomolec. Spectr. 53:381-392.
23. Dokter, A. M., M. C. van Hemert, C. M. In 't Velt, K. van der Hoef, J. Lugtenburg, H. A. Frank, and E. J. J. Groenen. 2002. Resonance Raman spectrum of all-trans-spheroidene. DFT analysis and isotope labeling. J. Phys. Chem. A. 106:9463-9469.
24. Gebhard, R., K. van der Hoef, A. W. M. Lefeber, C. Erkelens, and J. Lugtenburg. 1990. Synthesis and spectroscopy of (14′-C-13)spheroidene and (15′-C-13)spheroidene. Recl. Trav. Chim. Pays-Bas-J. Roy. Neth. Chem. Soc. 109:378-387.
25. Gebhard, R., K. van der Hoef, C. A. Violette, H. J. M. de Groot, H. A. Frank, and J. Lugtenburg. 1991. C-13 magic angle spinning NMR evidence for a 15,15′-z configuration of the spheroidene chromophore in the Rhodobacter-sphaeroides reaction center - synthesis of C-13-labeled and H-2-labeled spheroidenes. Pure Appl. Chem. 63:115-122.
26. Gebhard, R., J. T. M. van Dijk, M. V. T. J. Boza, K. van der Hoef, and J. Lugtenburg. 1991. Synthesis and spectroscopic properties of 14-monodeuterospheroidenes, 15-monodeuterospheroidenes, 15′- monodeuterospheroidenes and 14′-monodeuterospheroidenes and 15,15′-dideuterospheroidenes. Recl. Trav. Chim. Pays-Bas-J. Roy. Neth. Chem. Soc. 110:332-341.
27. Gebhard, R., J. T. M. van Dijk, E. van Ouwerkerk, M. V. T. J. Boza, and J. Lugtenburg. 1991. Synthesis and spectroscopy of chemically modified spheroidenes. Recl. Trav. Chim. Pays-Bas-J. Roy. Neth. Chem. Soc. 110:459-469.
28. Curry, B., I. Palings, A. D. Broek, J. A. Pardoen, J. Lugtenburg, and R. Mathies. 1985. Advances in Infrared and Raman Spectroscopy, Vol. 12, Chapt. 3. Wiley-Heyden, New York.
29. Frisch, M. J., G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople. 2003. Gaussian 03, Rev. B.05. Gaussian, Pittsburgh, PA.
30. Rauhut, G., and P. Pulay. 1995. Transferable scaling factors for density functional derived vibrational force fields. J. Phys. Chem. 99:3093-3100.
31. Myers, A. B., R. A. Harris, and R. A. Mathies. 1983. Resonance Raman excitation profiles of bacteriorhodopsin. J. Chem. Phys. 79:603-613.
32. Wirtz, A. C. 2006. Probing structure and organization. PhD thesis. Leiden University, Casimir Research School, Delft-Leiden. ISBN-13: 978-90-8593-017-4.
33. Kolaczkowski, S. V. 1989. On the mechanism of triplet energy transfer from the triplet primary donor to spheroidene in photosynthetic reaction centers from Rhodobacter sphaeroides 2.4.1. PhD thesis. Brown University, Providence, RI.
34. Kakitani, Y., R. Fujii, Y. Koyama, H. Nagae, L. Walker, B. Salter, and A. Angerhofer. 2006. Triplet-state conformational changes in 15-cis-spheroidene bound to the reaction center from Rhodobacter sphaeroides 2.4.1 as revealed by time-resolved EPR spectroscopy: strengthened hypothetical mechanism of triplet-energy dissipation. Biochemistry. 45:2053-2062.