Self-aggregates of bacteriochlorophylls-c, d and e in a light-harvesting antenna system of green photosynthetic bacteria: Effect of stereochemistry at the chiral 3-(1-hydroxyethyl) group on the supramolecular arrangement of chlorophyllous pigments

Journal of Photochemistry and Photobiology C: Photochemistry Reviews

Volumn 6, Issue 2-3, 2005, Pages 89-107

  Miyatake, Tomohiro ^a   Tamiaki, Hitoshi ^b  

^a RYUKOKU UNIVERSITY   (Japan)

^b RITSUMEIKAN UNIVERSITY   (Japan)

Author keywords

Antenna; Chirality; Chlorophyll; Photosynthesis; Self assembly

Indexed keywords

CHLOROPHYLL; CHROMOSOMES; PHOTOSYNTHESIS; SELF ASSEMBLY; STEREOCHEMISTRY;

CHIRALITY; LIGHT-HARVESTING ANTENNA SYSTEMS; SELF-AGGREGATION; STEREOCHEMICAL CONTROL;

BACTERIA;

EID: 25444505748     PISSN: 13895567     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochemrev.2005.06.001     Document Type: Review

References (113)

1. T. Oba, H. Tamiaki, Bioorg. Med. Chem. 13 (2005) in press.
2. T. Oba, and H. Tamiaki Photosynth. Res. 74 2002 1 10
3. T.S. Balaban, H. Tamiaki, A.R. Holzwarth, in: F. Würthner (Ed.), Supramolecular Dye Chemistry, Topics in Current Chemistry, vol. 258, Springer, Heidelberg, 2005, in press.
4. R.E. Blankenship, and K. Matsuura B.R. Green W.W. Parson Light-Harvesting Antennas in Photosynthesis 2003 Kluwer Academic Publishers Dordrecht 195 217
5. B. Ke Photosynthesis: Photobiochemistry and Photobiophysics 2001 Kluwer Academic Publishers Dordrecht pp. 147-158
6. J.M. Olson Photochem. Photobiol. 67 1998 61 75
7. H. Tamiaki Coord. Chem. Rev. 148 1996 183 197
8. R.E. Blankenship, J.M. Olson, and M. Miller R.E. Blankenship M.T. Madigan C.E. Bauer Anoxygenic Photosynthetic Bacteria 1995 Kluwer Academic Publishers Dordrecht 399 435
9. A.R. Holzwarth, K. Griebenow, and K. Schaffner J. Photochem. Photobiol. A: Chem. 65 1992 61 71
10. H. Tamiaki, M. Amakawa, Y. Shimono, R. Tanikaga, A.R. Holzwarth, and K. Schaffner Photochem. Photobiol. 63 1996 92 99
11. P. Hildebrandt, H. Tamiaki, A.R. Holzwarth, and K. Schaffner J. Phys. Chem. 98 1994 2192 2197
12. H. Scheer B.R. Green W.W. Parson Light-Harvesting Antennas in Photosynthesis 2003 Kluwer Academic Publishers Dordrecht 29 81
13. T. Oba, and H. Tamiaki Photosynth. Res. 61 1999 23 31
14. K.M. Smith, L.A. Kehres, and J. Fajer J. Am. Chem. Soc. 105 1983 1387 1389
15. M.I. Bystrova, I.N. Mal'gosheva, and A.A. Krasnovskii Mol. Biol. 13 1979 440 451
16. V.I. Prokhorenko, D.B. Steensgaard, and A.R. Holzwarth Biophys. J. 85 2003 3173 3186
17. T.S. Balaban, A.R. Holzwarth, and K. Schaffner J. Mol. Struct. 349 1995 183 186
18. K. Griebenow, A.R. Holzwarth, F. van Mourik, and R. van Grondelle Biochim. Biophys. Acta 1058 1991 194 202
19. L.A. Staehelin, J.R. Golecki, and G. Drews Biochim. Biophys. Acta 589 1980 30 45
20. L.A. Staehelin, J.R. Golecki, R.C. Fuller, and G. Drews Arch. Microbiol. 119 1978 269 277
21. D.B. Steensgaard, H. Wackerbarth, P. Hildebrandt, and A.R. Holzwarth J. Phys. Chem. B 104 2000 10379 10386
22. V.I. Prokhorenko, D.B. Steensgaard, and A.R. Holzwarth Biophys. J. 79 2000 2105 2120
23. T. Nozawa, K. Ohtomo, M. Suzuki, H. Nakagawa, Y. Shikama, H. Konami, and Z.-Y. Wang Photosynth. Res. 41 1994 211 223
24. A.R. Holzwarth, and K. Schaffner Photosynth. Res. 41 1994 225 233
25. K. Matsuura, M. Hirota, K. Shimada, and M. Mimuro Photochem. Photobiol. 57 1993 92 97
26. J. Pšenčík, T.P. Ikonen, P. Laurinmäki, M.C. Merckel, S.J. Butcher, R.E. Serimaa, and R. Tuma Biophys. J. 87 2004 1165 1172
27. H. Tamiaki, H. Kitamoto, A. Nishikawa, T. Hibino, and R. Shibata Bioorg. Med. Chem. 12 2004 1657 1666
28. H. Tamiaki, A.R. Holzwarth, and K. Schaffner Photosynth. Res. 41 1994 245 251
29. K.M. Smith K.M. Kadish K.M. Smith R. Guilard The Porphyrin Handbook vol. 13 2003 Academic Press San Diego 157 182
30. K.M. Smith Photosynth. Res. 41 1994 23 26
31. F. Fages, N. Griebenow, K. Griebenow, A.R. Holzwarth, and K. Schaffner J. Chem. Soc. Perkin Trans. 1 1990 2791 2797
32. T. Mizoguchi, Y. Saga, and H. Tamiaki Photochem. Photobiol. Sci. 1 2002 780 787
33. Y. Saga, K. Matsuura, and H. Tamiaki Photochem. Photobiol. 74 2001 72 80
34. C.M. Borrego, and L.J. Garcia-Gil Photosynth. Res. 41 1994 157 163
35. F.W. Bobe, N. Pfennig, K.L. Swanson, and K.M. Smith Biochemistry 29 1990 4340 4348
36. K.M. Smith, and F.W. Bobe J. Chem. Soc. Chem. Commun. 1987 276 277
37. K.M. Smith, and D.A. Goff J. Chem. Soc. Perkin Trans. 1 1985 1099 1113
38. K.M. Smith, and D.A. Goff J. Am. Chem. Soc. 105 1983 1674 1676
39. M.B. Caple, H.-C. Chow, and C.E. Strouse J. Biol. Chem. 253 1978 6730 6737
40. H. Tamiaki, S. Takeuchi, S. Tsudzuki, T. Miyatake, and R. Tanikaga Tetrahedron 54 1998 6699 6718
41. K.M. Smith, and D.A. Goff J. Am. Chem. Soc. 104 1982 3747 3749
42. K.M. Smith, L.A. Kehres, and H.D. Tabba J. Am. Chem. Soc. 102 1980 7149 7151
43. K.M. Smith, G.M.F. Bisset, and M.J. Bushell J. Org. Chem. 45 1980 2218 2224
44. T. Miyatake, T. Oba, and H. Tamiaki ChemBiolChem 2 2001 335 342
45. R.L. Airs, and B.J. Keely Rapid Commun. Mass Spectrom. 16 2002 453 461
46. N. Risch, and H. Brockmann Jr. Liebigs Ann. Chem. 1976 578 583
47. H. Brockmann Jr., and R. Tacke-Karimdadian Liebigs Ann. Chem. 1979 419 430
48. T. Mizoguchi, H. Oh-oka, H. Tamiaki, Photochem. Photobiol. 81 (2005) 666-673.
49. N.-U. Frigaard, A.G.M. Chew, H. Li, J.A. Maresca, and D.A. Bryant Photosynth. Res. 78 2003 93 117
50. H. Tamiaki, M. Kouraba, K. Takeda, S. Kondo, and R. Tanikaga Tetrahedron: Asymmetr. 9 1998 2101 2111
51. H. Tamiaki, Photochem. Photobiol. Sci. 4 (2005) in press.
52. C.M. Borrego, P.D. Gerola, M. Miller, and R.P. Cox Photosynth. Res. 59 1999 159 166
53. C.M. Borrego, and L.J. Garcia-Gil Photosynth. Res. 45 1995 21 30
54. T. Ishii, M. Kimura, T. Yamamoto, M. Kirihata, and K. Uehara Photochem. Photobiol. 71 2000 567 573
55. M. Hirota, T. Moriyama, K. Shimada, M. Miller, J.M. Olson, and K. Matsuura Biochim. Biophys. Acta 1099 1992 271 274
56. M. Miller, T. Gillbro, and J.M. Olson Photochem. Photobiol. 57 1993 98 102
57. K. Uehara, M. Mimuro, Y. Ozaki, and J.M. Olson Photosynth. Res. 41 1994 235 243
58. T. Miyatake, H. Tamiaki, M. Fujiwara, and T. Matsushita Bioorg. Med. Chem. 12 2004 2173 2178
59. T. Miyatake, H. Tamiaki, A.R. Holzwarth, and K. Schaffner Helv. Chim. Acta 82 1999 797 810
60. A. Planner, J. Goc, A. Dudkowiak, D. Fra̧ckowiak, and J. Miyake J. Photochem. Photobiol. B 39 1997 73 80
61. H. Möltgen, K. Kleinermanns, A. Jesorka, K. Schaffner, and A.R. Holzwarth Photochem. Photobiol. 75 2002 619 626
62. I. de Boer, J. Matysik, K. Erkelens, S. Sasaki, T. Miyatake, S. Yagai, H. Tamiaki, A.R. Holzwarth, and H.J.M. de Groot J. Phys. Chem. B 108 2004 16556 16566
63. I. de Boer, J. Matysik, M. Amakawa, S. Yagai, H. Tamiaki, A.R. Holzwarth, and H.J.M. de Groot J. Am. Chem. Soc. 125 2003 13374 13375
64. A. Dudkowiak, C. Francke, J. Amesz, A. Planner, and D. Fra̧ckowiak Spectrochim. Acta A 52 1996 1661 1669
65. A. Dudkowiak, C. Francke, J. Amesz, A. Planner, I. Hanyz, and D. Fra̧ckowiak Spectrochim. Acta A 52 1996 251 264
66. T. Martyìski, D. Fra̧ckowiak, J. Miyake, A. Dudkowiak, and A. Piechowiak J. Photochem. Photobiol. B 42 1998 57 66
67. D. Fra̧ckowiak, A. Dudkowiak, A. Ptak, H. Malak, I. Gryczyński, and B. Zelent J. Photochem. Photobiol. B 44 1998 231 239
68. K.M. Smith, F.W. Bobe, D.A. Goff, and R.J. Abraham J. Am. Chem. Soc. 108 1986 1111 1120
69. M. Umetsu, R. Seki, Z.-Y. Wang, I. Kumagai, and T. Nozawa J. Phys. Chem. B 106 2002 3987 3995
70. Z.-Y. Wang, M. Umetsu, M. Kobayashi, and T. Nozawa J. Phys. Chem. B 103 1999 3742 3753
71. Z.-Y. Wang, M. Umetsu, M. Kobayashi, and T. Nozawa J. Am. Chem. Soc. 121 1999 9363 9369
72. T. Mizoguchi, K. Ogura, F. Inagaki, and Y. Koyama Biospectroscopy 5 1999 63 77
73. T. Mizoguchi, K. Hara, H. Nagae, and Y. Koyama Photochem. Photobiol. 71 2000 596 609
74. T.S. Balaban, H. Tamiaki, A.R. Holzwarth, and K. Schaffner J. Phys. Chem. B 101 1997 3424 3431
75. M. Umetsu, J.G. Hollander, J. Matysik, Z.-Y. Wang, T. Adschiri, T. Nozawa, and H.J.M. de Groot J. Phys. Chem. B 108 2004 2726 2734
76. Z.-Y. Wang, T. Kadota, M. Kobayashi, A. Kasuya, and T. Nozawa J. Phys. Chem. B 108 2004 15422 15428
77. Q.-M. Xu, L.-J. Wan, S.-X. Yin, C. Wang, C.-L. Bai, T. Ishii, K. Uehara, Z.-Y. Wang, and T. Nozawa J. Phys. Chem. B 106 2002 3037 3040
78. T.S. Balaban, J. Leitich, A.R. Holzwarth, and K. Schaffner J. Phys. Chem. B 104 2000 1362 1372
79. T. Ishii, K. Uehara, Y. Ozaki, and M. Mimuro Photochem. Photobiol. 70 1999 760 765
80. M. Umetsu, Z.-Y. Wang, J. Zhang, T. Ishii, K. Uehara, Y. Inoko, M. Kobayashi, and T. Nozawa Photosynth. Res. 60 1999 229 239
81. M. Umetsu, Z.-Y. Wang, M. Kobayashi, and T. Nozawa Biochim. Biophys. Acta 1410 1999 19 31
82. A. Dudkowiak, C. Francke, and J. Amesz Photosynth. Res. 46 1995 427 433
83. T. Mizoguchi, K. Matsuura, K. Shimada, and Y. Koyama Chem. Phys. Lett. 260 1996 153 158
84. T. Mizoguchi, S. Sakamoto, Y. Koyama, K. Ogura, and F. Inagaki Photochem. Photobiol. 67 1998 239 248
85. P. Cheng, P.A. Liddell, S.X.C. Ma, and R.E. Blankenship Photochem. Photobiol. 58 1993 290 295
86. H. Tamiaki, S. Takeuchi, R. Tanikaga, T.S. Balaban, A.R. Holzwarth, and K. Schaffner Chem. Lett. 1994 401 402
87. H. Tamiaki, H. Kitamoto, T. Watanabe, and R. Shibata Photochem. Photobiol. 81 2005 170 176
88. J. Chiefari, K. Griebenow, N. Griebenow, T.S. Balaban, A.R. Holzwarth, and K. Schaffner J. Phys. Chem. 99 1995 1357 1365
89. M. Umetsu, R. Seki, T. Kadota, Z.-Y. Wang, T. Adschiri, and T. Nozawa J. Phys. Chem. B 107 2003 9876 9882
90. B.-J. van Rossum, D.B. Steensgaard, F.M. Mulder, G.J. Boender, K. Schaffner, A.R. Holzwarth, and H.J.M. de Groot Biochemistry 40 2001 1587 1595
91. S. Yagai, T. Miyatake, Y. Shimono, and H. Tamiaki Photochem. Photobiol. 73 2001 153 163
92. T. Miyatake, K. Shitasue, Y. Omori, K. Nakagawa, M. Fujiwara, T. Matsushita, H. Tamiaki, Photosynth. Res. (2005) in press.
93. N. Wakao, N. Yokoi, N. Isoyama, A. Hiraishi, K. Shimada, M. Kobayashi, H. Kise, M. Iwaki, S. Itoh, S. Takaichi, and Y. Sakurai Plant Cell Physiol. 37 1996 889 893
94. V.I. Prokhorenko, A.R. Holzwarth, M.G. Müller, K. Schaffner, T. Miyatake, and H. Tamiaki J. Phys. Chem. B 106 2002 5761 5768
95. T. Miyatake, H. Tamiaki, A.R. Holzwarth, and K. Schaffner Photochem. Photobiol. 69 1999 92 99
96. H. Tamiaki, T. Miyatake, R. Tanikaga, A.R. Holzwarth, and K. Schaffner Angew. Chem. Int. Ed. 35 1996 772 774
97. H. Tamiaki, M. Kubo, and T. Oba Tetrahedron 56 2000 6245 6257
98. D.J. Simpson, and K.M. Smith J. Am. Chem. Soc. 110 1988 1753 1758
99. H. Tamiaki, M. Omoda, Y. Saga, and H. Morishita Tetrahedron 59 2003 4337 4350
100. H. Tamiaki, M. Omoda, and M. Kubo Bioorg. Med. Chem. Lett. 9 1999 1631 1632
101. U. Feiler, A. Delphine, M. Lutz, and B. Robert Photosynth. Res. 41 1994 175 180
102. S. Sasaki, and H. Tamiaki Bull. Chem. Soc. Jpn. 77 2004 797 800
103. S. Sasaki, M. Omoda, and H. Tamiaki J. Photochem. Photobiol. A: Chem. 162 2004 307 315
104. H. Tamiaki, H. Kiatamoto, A. Nishikawa, T. Hibino, R. Shibata, in: Science Program Committee of ISBC2003 (Ed.), Biomolecular Chemistry - A Bridge for the Future, Maruzen, Tokyo, 2003, pp. 184-187.
105. S. Yagai, T. Miyatake, and H. Tamiaki J. Org. Chem. 67 2002 49 58
106. H. Tamiaki, T. Miyatake, and R. Tanikaga Tetrahedron Lett. 38 1997 267 270
107. A. Jesorka, T.S. Balaban, A.R. Holzwarth, and K. Schaffner Angew. Chem. Int. Ed. 35 1996 2861 2863
108. H. Tamiaki, T. Kubota, and R. Tanikaga Chem. Lett. 1996 639 640
109. M. Kunieda, T. Mizoguchi, and H. Tamiaki Photochem. Photobiol. 79 2004 55 61
110. H. Tamiaki, T. Watanabe, and T. Miyatake J. Porphyrins Phthalocyan. 3 1999 45 52
111. T.S. Balaban, M. Linke-Schaetzel, A.D. Bhise, N. Vanthuyne, and C. Roussel Eur. J. Org. Chem. 2004 3919 3930
112. T.S. Balaban, A.D. Bhise, M. Fisher, M. Linke-Schaetzel, C. Roussel, and N. Vanthuyne Angew. Chem. Int. Ed. 42 2003 2140 2144
113. H. Tamiaki, S. Kimura, and T. Kimura Tetrahedron 59 2003 7423 7435