Self-assembly of methyl zinc (31R)- and (31S)-bacteriopheophorbides d

Journal of Physical Chemistry B

Volumn 101, Issue 17, 1997, Pages 3424-3431

  Balaban, Teodor Silviu ^a   Tamiaki, Hitoshi ^b   Holzwarth, Alfred R ^a   Schaffner, Kurt ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

^b RITSUMEIKAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000034022     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp962872m     Document Type: Article

References (49)

1. 2) of particularly intriguing structural beauty: McDermott, G.; Prince, S. M.; Freer, A. A.; Hawthornthwaite-Lawless, A. M.; Papiz, M. Z.; Cogdell, R. J.; Isaacs, N. W. Nature 1995, 374, 517-521. Koepke, J.; Hu, X.; Muenke, C.; Schulten, K.; Michel, H. Structure 1996, 4, 581-597.
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4. For reviews see: Tamiaki, H. Coord. Chem. Rev. 1996,148, 183-197. Blankenship, R. E.; Olson, J. M.; Miller, M. In Anoxygenic Pholosynlhetic Bacteria; Blankenship, R. E.; Madigan, M. T., Bauer, C. E., Eds.; Kluwer Academic Publishers: Dordrecht, 1995; pp 399-435.
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7. Holzwarth, A. R.; Griebenow, K.; Schaffner, K. Z. Naturforsch. 1990, 45c, 203-206. Griebenow, K.; Holzwarth, A. R.; Schaffner. K. lbid. 823-828. Holzwarth, A. R.; Griebenow, K.; Schaffner K. J. Photochem. Photobiol. A: Chem. 1992, 65, 61-71.
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15. Tamiaki, H.; Miyatake, T.; Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Angew. Chem. 1996, 108, 810-812; Angew. Chem., Int. Ed. Engl. 1996, 35, 772-774.
16. Tamiaki, H.; Miyatake, T.; Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Angew. Chem. 1996, 108, 810-812; Angew. Chem., Int. Ed. Engl. 1996, 35, 772-774.
17. Chiefari, J.; Griebenow, K.; Fages, F.; Griebenow, N.; Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. J. Phys. Chem. 1995, 99, 1357-1365.
18. (a) Hildebrandt, Griebenow, K.; Holzwarth, A. R.; Schaffner, K. Z. Naturforsch. 1991, 46c, 228-232.
19. (b) Hildebrandt, P.; Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. J. Phys. Chem. 1994, 98, 2192-2197.
20. Balaban, T. S.; Holzwarth, A. R.; Schaffner, K.; Boender, G.-J.; de Groot, H. J. M. Biochemistry 1995, 34, 15259-15266.
21. For modifications of the nature and the positions of these functional groups see: (a) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. J. Photochem. Photobiol. B: Biol. 1992, 15, 355-360. (b) Tamiaki, H.; Amakawa. M.; Shimono, Y.; Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Photochem. Photobiol. 1996, 63, 92-99. (c) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. Photosynth. Res. 1994, 41, 245-251. (d) Jesorka, A.; Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. Angew. Chem. 1996, 108, 3019-3021; Angew. Chem., Int. Ed. Engl. 1996, 35, 2861-2863. (e) Tamiaki, H.; Kubota, T.; Tanikaga, R. Chem. Lett. 1996, 639-640. (f) Tamiaki, H.; Shimono, Y.; Rattray, A. G. M.; Tanikaga, R. Bioorg. Med. Chem. Lett. 1996, 6, 2085-2086. (g) Tamiaki, H.; Miyata, S.; Kureishi, Y.; Tanikaga, R. Tetrahedron 1996, 52, 12421-12432.
22. For modifications of the nature and the positions of these functional groups see: (a) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. J. Photochem. Photobiol. B: Biol. 1992, 15, 355-360. (b) Tamiaki, H.; Amakawa. M.; Shimono, Y.; Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Photochem. Photobiol. 1996, 63, 92-99. (c) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. Photosynth. Res. 1994, 41, 245-251. (d) Jesorka, A.; Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. Angew. Chem. 1996, 108, 3019-3021; Angew. Chem., Int. Ed. Engl. 1996, 35, 2861-2863. (e) Tamiaki, H.; Kubota, T.; Tanikaga, R. Chem. Lett. 1996, 639-640. (f) Tamiaki, H.; Shimono, Y.; Rattray, A. G. M.; Tanikaga, R. Bioorg. Med. Chem. Lett. 1996, 6, 2085-2086. (g) Tamiaki, H.; Miyata, S.; Kureishi, Y.; Tanikaga, R. Tetrahedron 1996, 52, 12421-12432.
23. For modifications of the nature and the positions of these functional groups see: (a) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. J. Photochem. Photobiol. B: Biol. 1992, 15, 355-360. (b) Tamiaki, H.; Amakawa. M.; Shimono, Y.; Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Photochem. Photobiol. 1996, 63, 92-99. (c) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. Photosynth. Res. 1994, 41, 245-251. (d) Jesorka, A.; Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. Angew. Chem. 1996, 108, 3019-3021; Angew. Chem., Int. Ed. Engl. 1996, 35, 2861-2863. (e) Tamiaki, H.; Kubota, T.; Tanikaga, R. Chem. Lett. 1996, 639-640. (f) Tamiaki, H.; Shimono, Y.; Rattray, A. G. M.; Tanikaga, R. Bioorg. Med. Chem. Lett. 1996, 6, 2085-2086. (g) Tamiaki, H.; Miyata, S.; Kureishi, Y.; Tanikaga, R. Tetrahedron 1996, 52, 12421-12432.
24. For modifications of the nature and the positions of these functional groups see: (a) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. J. Photochem. Photobiol. B: Biol. 1992, 15, 355-360. (b) Tamiaki, H.; Amakawa. M.; Shimono, Y.; Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Photochem. Photobiol. 1996, 63, 92-99. (c) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. Photosynth. Res. 1994, 41, 245-251. (d) Jesorka, A.; Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. Angew. Chem. 1996, 108, 3019-3021; Angew. Chem., Int. Ed. Engl. 1996, 35, 2861-2863. (e) Tamiaki, H.; Kubota, T.; Tanikaga, R. Chem. Lett. 1996, 639-640. (f) Tamiaki, H.; Shimono, Y.; Rattray, A. G. M.; Tanikaga, R. Bioorg. Med. Chem. Lett. 1996, 6, 2085-2086. (g) Tamiaki, H.; Miyata, S.; Kureishi, Y.; Tanikaga, R. Tetrahedron 1996, 52, 12421-12432.
25. For modifications of the nature and the positions of these functional groups see: (a) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. J. Photochem. Photobiol. B: Biol. 1992, 15, 355-360. (b) Tamiaki, H.; Amakawa. M.; Shimono, Y.; Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Photochem. Photobiol. 1996, 63, 92-99. (c) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. Photosynth. Res. 1994, 41, 245-251. (d) Jesorka, A.; Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. Angew. Chem. 1996, 108, 3019-3021; Angew. Chem., Int. Ed. Engl. 1996, 35, 2861-2863. (e) Tamiaki, H.; Kubota, T.; Tanikaga, R. Chem. Lett. 1996, 639-640. (f) Tamiaki, H.; Shimono, Y.; Rattray, A. G. M.; Tanikaga, R. Bioorg. Med. Chem. Lett. 1996, 6, 2085-2086. (g) Tamiaki, H.; Miyata, S.; Kureishi, Y.; Tanikaga, R. Tetrahedron 1996, 52, 12421-12432.
26. For modifications of the nature and the positions of these functional groups see: (a) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. J. Photochem. Photobiol. B: Biol. 1992, 15, 355-360. (b) Tamiaki, H.; Amakawa. M.; Shimono, Y.; Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Photochem. Photobiol. 1996, 63, 92-99. (c) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. Photosynth. Res. 1994, 41, 245-251. (d) Jesorka, A.; Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. Angew. Chem. 1996, 108, 3019-3021; Angew. Chem., Int. Ed. Engl. 1996, 35, 2861-2863. (e) Tamiaki, H.; Kubota, T.; Tanikaga, R. Chem. Lett. 1996, 639-640. (f) Tamiaki, H.; Shimono, Y.; Rattray, A. G. M.; Tanikaga, R. Bioorg. Med. Chem. Lett. 1996, 6, 2085-2086. (g) Tamiaki, H.; Miyata, S.; Kureishi, Y.; Tanikaga, R. Tetrahedron 1996, 52, 12421-12432.
27. For modifications of the nature and the positions of these functional groups see: (a) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. J. Photochem. Photobiol. B: Biol. 1992, 15, 355-360. (b) Tamiaki, H.; Amakawa. M.; Shimono, Y.; Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Photochem. Photobiol. 1996, 63, 92-99. (c) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. Photosynth. Res. 1994, 41, 245-251. (d) Jesorka, A.; Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. Angew. Chem. 1996, 108, 3019-3021; Angew. Chem., Int. Ed. Engl. 1996, 35, 2861-2863. (e) Tamiaki, H.; Kubota, T.; Tanikaga, R. Chem. Lett. 1996, 639-640. (f) Tamiaki, H.; Shimono, Y.; Rattray, A. G. M.; Tanikaga, R. Bioorg. Med. Chem. Lett. 1996, 6, 2085-2086. (g) Tamiaki, H.; Miyata, S.; Kureishi, Y.; Tanikaga, R. Tetrahedron 1996, 52, 12421-12432.
28. For modifications of the nature and the positions of these functional groups see: (a) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. J. Photochem. Photobiol. B: Biol. 1992, 15, 355-360. (b) Tamiaki, H.; Amakawa. M.; Shimono, Y.; Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Photochem. Photobiol. 1996, 63, 92-99. (c) Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. Photosynth. Res. 1994, 41, 245-251. (d) Jesorka, A.; Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. Angew. Chem. 1996, 108, 3019-3021; Angew. Chem., Int. Ed. Engl. 1996, 35, 2861-2863. (e) Tamiaki, H.; Kubota, T.; Tanikaga, R. Chem. Lett. 1996, 639-640. (f) Tamiaki, H.; Shimono, Y.; Rattray, A. G. M.; Tanikaga, R. Bioorg. Med. Chem. Lett. 1996, 6, 2085-2086. (g) Tamiaki, H.; Miyata, S.; Kureishi, Y.; Tanikaga, R. Tetrahedron 1996, 52, 12421-12432.
29. (a) Holzwarth, A. R.; Schaffner, K. Photosynth. Res. 1994, 41, 225-233.
30. (b) Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. In preparation.
31. 5b (i.e., HO⋯M stacking) and Worcester et al. (C=O⋯H-O⋯M): Worcester, D. L.; Michalski, T. J.; Katz, J. J. Proc. Natl. Acad. Sci. USA. 1986, 83, 3791-3795. They have been tentatively expanded later: Brune, D. C.; King, G. H.; Blankenship, R. E. In Photosynthetic Light-harvesting Svstems; Scheer, H., Schneider, S., Eds.; Walter de Gruyter: Berlin, 1988; pp 141-151.
32. 5b (i.e., HO⋯M stacking) and Worcester et al. (C=O⋯H-O⋯M): Worcester, D. L.; Michalski, T. J.; Katz, J. J. Proc. Natl. Acad. Sci. USA. 1986, 83, 3791-3795. They have been tentatively expanded later: Brune, D. C.; King, G. H.; Blankenship, R. E. In Photosynthetic Light-harvesting Svstems; Scheer, H., Schneider, S., Eds.; Walter de Gruyter: Berlin, 1988; pp 141-151.
33. 13,16
34. Staehelin, L. A.; Golecki, J. R.; Fuller, R. C.; Drews, G. Arch. Mitrobiol. 1978, 119, 269-277.
35. Worcester, D. L.; Michalski, T. J.; Bowman, M. K.; Katz, J. J. Mat. Res. Soc. Symp. Proc. 1990, 174, 157-161.
36. See ref 8 for the definition of type I and II BChl c aggregates, and ref 18 for the discussion of the corresponding scheme for BChl monomer - aggregate equilibria.
37. Balaban, T. S.; Leitich, J.; Holzwarth, A. R.; Schaffner, K. To be submitted.
38. 20
39. Tamiaki, H.; Takeuchi, S.; Tanikaga, R.; Balaban, S. T.; Holzwarth, A. R.; Schaffner, K. Chem. Lett. 1994, 401-402.
40. Balaban, T. S.; Holzwarth, A. R.; Schaffner, K. J. Mol. Struct. 1995, 349, 183-186.
41. Wakao, N.; Yokoi, N.; lsoyama, N.; Hiraiashi, A.; Shimada, K.; Kobayashi, M.; Kise, H.; Iwaki, M.; Itoh, S.; Takaichi, S.; Sakurai, Y. Plant Cell Plnsiol. 1996, 37, 889-893.
42. Fujiwara, M., Tasumi, M. J. Phys. Chem. 1986, 90, 5646-5650.
43. Abraham, R. J.; Smith, K. M.; Goff, D. A.; Bobe, F. W. J. Am. Chem. Soc. 1985, 107, 1085-1087. Smith, K. M.; Bobe, F. W.; Goff, D. A; Abraham, R. J. lbid. 1986, 108. 1111 -1120.
44. Abraham, R. J.; Smith, K. M.; Goff, D. A.; Bobe, F. W. J. Am. Chem. Soc. 1985, 107, 1085-1087. Smith, K. M.; Bobe, F. W.; Goff, D. A; Abraham, R. J. lbid. 1986, 108. 1111 -1120.
45. 1-hydroxy group coordinates with the central metal atom of the opposite dimer half. In open dimers only one of the hydroxyls coordinates with the metal of the other half.
46. F has shown, by inlermolccular NOE, a nonsymmetrical closed dimer to occur at room temperature in chloroform containing a certain amount of methanol: Mizoguchi, T.; Limantara, L.; Matsuura, K.; Shimada, K.; Koyama, Y. J. Mol. Struct. 1996, 379, 249-265. This result is not at variance with our conclusions. Rather, it illustrates the diversity of aggregated species formed as a function of solvent nature, temperature, and concentration.
47. Slightly simplified versions of Scheme 1 have been presented in refs 8 and 11c.
48. A detailed assignment of the vis absorptions to the closed dimers and their oligomers appears premature at present.
49. 14 arise from open dimers by a combination of stack extension and stack pairing. The parent building blocks formed in these processes are exemplified in Figure 11 at the level of tetramers.