Metal-substituted bacteriochlorophylls. 1. Preparation and influence of metal and coordination on spectra

Journal of the American Chemical Society

Volumn 120, Issue 15, 1998, Pages 3675-3683

  Hartwich, Gerhard ^a,b   Fiedor, Leszek ^c,e   Simonin, Ingrid ^b   Cmiel, Edmund ^a   Schäfer, Wolfgang ^d   Noy, Dror ^c   Scherz, Avigdor ^c   Scheer, Hugo ^b  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF MUNICH   (Germany)

^c WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^d MAX PLANCK INSTITUTE OF BIOCHEMISTRY   (Germany)

^e JAGIELLONIAN UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; BACTERIOCHLORIN; BACTERIOCHLOROPHYLL; BACTERIOPHEOPHYTIN; CADMIUM; COBALT; COPPER ION; MANGANESE; METAL; NICKEL; PALLADIUM; ZINC ION;

ARTICLE; FLUORESCENCE SPECTROSCOPY; LIGAND BINDING; MASS SPECTROMETRY; METAL BINDING; OXIDATION REDUCTION REACTION; PHOSPHORESCENCE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0032557225     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970874u     Document Type: Article

References (68)

1. For leading references, see: Chlorophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, 1991.
2. Spikes, J. D.; Sommer, J. C. In Chlorophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, 1991; pp 1181-1204.
3. Pandey, R. K.; Bellnier, D. A.; Smith, K. M.; Dougherty, T. J. Photochem. Photobiol. 1990, 53, 65-72.
4. Pandey, R. K.; Shiau, F. Y.; Sumlin, A. B.; Dougherty, T. J.; Smith, K. M. Bioorg. Med. Chem. Lett. 1994, 4. 1263-1267.
5. Moser, J. G.; Suchomski, R.; Danielowski, T.; Wagner, B.; Scheer, H.; Hartwich, G. SPIE Proceedings of the 5th Biennal Meeting IPA, Amelia Island FA 1995, 2371, 178-186.
6. Rosenbach-Belkin, V.; Chen, L.; Fiedor, L.; Tregub, I.; Pavlotsky, F.; Brumfeld, V.; Salomon, Y.; Scherz, A. Photochem. Photobiol. 1996, 64, 174-181.
7. Boyle, R. W.; Dolphin, D. Photochem. Photobiol. 1996, 64, 469-485.
8. Hyninnen, P. H. In Chlorophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, 1991; pp 145-209.
9. Watanabe, T.; Kobayashi, M. In Chlorophylls; Scheer, H., Ed.; CRC Press; Boca Raton, FL, 1991; pp 282-316.
10. Fajer, J.; Barkiga, K. M.; Smith, K. M.; Zhong, E.; Gudowska-Nowak, E.; Newton, N. D. In Reaction Centers of Photosynthetic Bacteria; Michel-Beyerle, M. E., Ed.; Springer-Verlag: Berlin, 1990; pp 367-376.
11. Barkiga, K. M.; Chamtranupong, L.; Smith, K. M.; Fajer, J. J. Am. Chem. Soc. 1988, 110, 7566-7567.
12. Renner, M. W.; Zhang, Y.; Noy, D.; Scherz, A.; Smith, K. M.; Fajer, J. In Reaction Centers of Photosynthetic Bacteria; Michel-Beyerle, M. E., Ed.; Springer-Verlag: Berlin, 1996; pp 367-376.
13. Buchler, J. W. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: New York, 1975; pp 157-232.
14. Gouterman, M.; Wagnière, G. H.; Snyder, L. C. J. Mol. Spectrosc. 1963, 11, 108-127.
15. Hanson, L. K. In Chlorophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, 1991; pp 993-1041.
16. (a) Losev, A. P.; Knyukshto, V. N.; Kochubeeva, N. D.; Solovev, K. N. Opt Spectrosc. 1991, 97, 97-101. This method did not work for us.
17. (b) Donohoe, R. J.; Frank, H. A.; Bocian, D. F. Photochem. Photobiol. 1988, 48, 531-537.
18. Hartwich, G. Dissertation Thesis, Technical University of München, 1994
19. Hartwich, G.; Friese, M.; Ogrodnik, A.; Scheer, H.; Michel-Beyerle, M. E. Chem. Phys. 1995, 197, 423-434.
20. Hartwich, G.; Geskes, C.; Scheer, H.; Heintze, J.; Mäntele, W. J. Am. Chem. Soc. 1995, 117, 7784-7790.
21. Hartwich, G.; Scheer, H.; Aust, V.; Angerhofer, A. Biochim. Biophys. Acta 1995, 1230, 97-113.
22. Scheer, H.; Hartwich G. In Anoxygenic Photosynthetic Bacteria; Blankenship, R. E., Madigan, M. T., Bauer, C. E., Eds.; Kluwer: Dordrecht, 1995; pp 649-664.
23. Geskes, C.; Hartwich, G.; Scheer, H.; Mäntele, W.; Heintze, J. J. Am. Chem. Soc. 1995, 117, 7776-7783.
24. Chen, L.; Wang, Z.; Hartwich, G.; Katheder, I.; Scheer, H.; Tiede, D. M.; Scherz, A.; Montano, P. A.; Norris, J. R. Chem. Phys. Lett. 1995, 234, 437-444.
25. Frank, H.; Chynwat, V.; Hartwich, G.; Meyer, M.; Katheder, I.; Scheer, H. Photosyn. Res. 1993, 37, 193-203.
26. Fiedor, L. Ph.D. Thesis, The Weizmann Institute of Science, Rehovot, Israel, 1994.
27. For leading references, see: Dolphin, D., Ed. The Porphyrms; Academic: New York, 1979; Vol. III, IV.
28. Strell, M.; Urumov, T. Liebigs Ann. Chem. 1977, 970-974.
29. Noy, D.; Fiedor, L.; Hartwich, G.; Scheer, H.; Scherz, A. J. Am. Chem. Soc. 1998, 120, 3684-3693.
30. 2-hydroxy derivates exhibit similar reactivities in the metalation reaction. Furthermore, such distortions are also expected to affect the BPhe optical absorption (ref 10), in contrast to what has been observed in our experiments.
31. Hambright, P. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier New York, 1975; pp 233-278.
32. Davis, D. G. In The Porphyrins; Dolphin, D., Ed.; Academic: New York, 1979; Vol. IV, pp 127-152.
33. Rodgers, A.; Hartwich, G.; Scheer, H. Unpublished results, 1996.
34. Takiff, L.; Boxer, S. G. Biochim. Biophys. Acta 1988, 932, 325-334.
35. Warshel, A.; Parson, W. W. J. Am. Chem. Soc. 1987, 109, 6143-6152.
36. Thompson, M. A.; Zerner, M. C.; Fajer, J. J. Phys. Chem. 1991, 95, 5693-5700.
37. 4h-symmetric metal-substituted porphyrins but is applicable to chlorins and bacteriochlorins despite reduced symmetry.
38. Scherz, A.; Fisher, J. R.; Braun, P. In Reaction Centers of Photosynthetic Bacteria; Michel-Beyerle, M. E., Ed.; Springer-Verlag: Berlin, 1990; pp 377-388.
39. Evans, T. A.; Katz, J. J. Biochim. Biophys. Acta 1975, 396, 414-426.
40. Callahan, P. M.; Cotton, T. M. J. Am. Chem. Soc. 1987, 109, 7001-7007.
41. y band to be resolved.
42. Scheidt, W. R. In The Porphyrins; Dolphin, D., Ed.; Academic: New York, 1979; Vol. III, pp 463-512.
43. 2+ is known to exhibit only quadratic planar coordination in porphyrins (ref 13).
44. Cotton, F. A.; Wilkinson, R. Advanced Inorganic Chemistry; Wiley: New York, 1988; 5th ed.
45. Scheer, H.; Struck, A. In The Photosynthetic Reaction Center; Norris, J. R., Deisenhofer, J., Eds.; Academic Press: New York, 1993; pp 157-192.
46. Gouterman, M. J. Chem. Phys. 1959, 30, 1139-1160.
47. Fuhrhop, J. H.; Kadish, K. M.; Davis, D. G. J. Am. Chem. Soc. 1973, 95, 5140-5152.
48. Mullay, J. In Structure and Bonding; Sen, K. D., Jorgensen, C. K., Eds.; Springer-Verlag: Berlin, 1987; Vol. 26, pp 1-26.
49. Alonso, J. A.; Balbas, L. C. In Structure and Bonding; Sen, K. D., Jorgensen, C. K., Eds.; Springer-Verlag; Berlin, 1987; Vol. 26, pp 41-78.
50. Harrison, R. D. Datenbuch Chemie Physik; Vieweg & Sohn; Braunschweig, 1982.
51. 2+ may not fit into the inner hole of the macrocycle and thus, deviate from the other [M]-BChls.
52. Deisenhofer, J.; Epp, O.; Miki, K.; Huber, R.; Michel, H. Nature 1985, 318, 618-624.
53. Ermler, U.; Fritzsch, G.; Buchanan, S. K.; Michel, H. Structure 1994, 2, 925-936.
54. x absorption (ref 22).
55. -1.
56. 3CN is not included into this comparison, since the chemical shifts of [M]-BChls are strongly dependent on the solvent.
57. Scheer, H.; Katz, J. J. J. Am. Chem. Soc. 1978, 100, 561-571.
58. Watanabe, T.; Machida, K.; Suzuki, H.; Kobayashi, M.; Honda, K. Coord. Chem. Rev. 1985, 64, 207-224.
59. Dougherty, R. C.; Strain, H. H.; Katz, J. J. J. Am. Chem. Soc. 1965, 87, 104-115.
60. Scheer, H.; Norris, J. R.; Katz, J. J. J. Am. Chem. Soc. 1977, 99, 1372-1381.
61. Senge, M. O.; Smith, K. M. Photochem. Photobiol. 1991, 54, 841-846.
62. Connick, P. A.; Haller, K. J.; Macor, K. A. Inorg. Chem. 1993, 32, 3256-3264.
63. York, D. M. Int. J. Quantum Chem. 1995, Suppl. 29.
64. Struck, A.; Cmiel, E.; Katheder, I.; Schäfer, W.; Scheer, H. Biochim. Biophys. Acta 1992, 1101, 321-328.
65. Omata, T.; Murata, N. Plant Cell Physiol. 1983, 24, 1093-1100.
66. Schaber, P. M.; Hunt, J. E.; Fries, R.; Katz, J. J. J. Chromatogr. 1984, 316, 25-41.
67. Pennington, F. C.; Strain, H. H.; Svec, W. A.; Katz, J. J. J. Am. Chem. Soc. 1964, 86, 1418-1426.
68. Rosenbach-Belkin, V. Ph.D. Thesis, The Weizmann Institut of Science, Rehovot, Israel, 1988.