Self-aggregation of synthetic zinc oxo-bacteriochlorins bearing substituents characteristic of chlorosomal chlorophylls

Journal of Organic Chemistry

Volumn 70, Issue 3, 2005, Pages 820-828

  Kunieda, Michio ^a   Tamiaki, Hitoshi ^a  

^a RITSUMEIKAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; AGGLOMERATION; BACTERIA; CHLOROPHYLL; COORDINATION REACTIONS; EXCITONS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROGEN BONDS; MATHEMATICAL MODELS; MOLECULAR DYNAMICS; REACTION KINETICS; SUPRAMOLECULAR CHEMISTRY;

CYCLOHEXANE; EXTRAMEMBRANES; PHOTOSYNTHETIC GREEN BACTERIA; STERIC EFFECTS;

CHLORINE COMPOUNDS;

7 ETHYL 7 METHYL 8 OXO BACTERIOCHLORIN; BACTERIOCHLORIN; CHLOROPHYLL; CYCLOHEXANE; UNCLASSIFIED DRUG; ZINC 8 ETHYL 8 METHYL 7 OXO BACTERIOCHLORIN;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL BOND; LIGHT HARVESTING SYSTEM; MOLECULAR MODEL; PHOTOSYNTHESIS; SUPRAMOLECULAR CHEMISTRY;

BACTERIOCHLOROPHYLLS; CHLOROFLEXUS; MODELS, CHEMICAL; PORPHYRINS; ZINC;

EID: 13244272101     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048263p     Document Type: Article

References (40)

1. (a) Olson, J. M. Photochem. Photobiol. 1998, 67, 61-75.
2. (b) Blankenship, R. E.; Matsuura, K. In Light Harvesting Antennas in Photosynthesis; Green, B. R., Parson, W. W., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2003; pp 195-217.
3. (c) Tamiaki, H. Coord. Chem. Rev. 1996, 148, 183-197.
4. Scheer, H. In Light Harvesting Antennas in Photosynthesis; Green, B. R., Parson, W. W., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2003; pp 29-81.
5. Holzwarth, A. R.; Schaffner, K. Photosynth. Res. 1994, 41, 225-233.
6. (a) Bystrova, M. I.; Mal'tgocheva, I. N.; Krasnovskii, A. A. Mol. Biol. 1979, 13, 440-451.
7. (b) Smith, K. M.; Kehres, L. A.; Fajer, J. J. Am. Chem. Soc. 1983, 105, 1387-1389.
8. (c) Brune, D. C.; Nozawa, T.; Blankenship, R. E. Biochemistry 1987, 26, 8644-8652.
9. (d) Balaban, T. S.; Leitich, J.; Holzwarth, A. R.; Schaffner, K. J. Phys. Chem. B 2000, 104, 1362-1372.
10. (e) Ishii, T.; Kimura, M.; Yamamoto, T.; Kirihata, M.; Uehara, K. Photochem. Photobiol. 2000, 71, 567-573.
11. (f) Mizoguchi, T.; Kara, K.; Nagae, H.; Koyama, Y. Photochem. Photobiol. 2000, 71, 596-609.
12. (g) Steensgaad, D. B.; Wacherbarth, H.; Hildebrandt, P.; Holzwarth, A. R. J. Phys. Chem. B 2000, 104, 10379-10386.
13. (h) Saga, Y.; Matsuura, K.; Tamiaki, H. Photochem. Photobiol. 2001, 74, 72-80.
14. (i) Mizoguchi, T.; Saga, Y.; Tamiaki, H. Photochem. Photobiol. Sci. 2002, 1, 780-787.
15. (j) Umetsu, M.; Hollander, J. G.; Matysik, J.; Wang, Z.-Y.; Adschiri, T.; Nozawa, T.; de Groot, H. J. M. J. Phys. Chem. B 2004, 108, 2726-2734.
16. (a) Tamiaki, H.; Amakawa, M.; Shimono, Y.; Tanikaga, R.; Holzwarth, A. R.; Schaffher, K. Photochem. Photobiol. 1996, 63, 92-99.
17. (b) Balaban, T. S.; Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. J. Phys. Chem. B 1997, 101, 3424-3431.
18. (c) Kureishi, Y.; Tamiaki, H. J. Porphyrins Phthalocyanines 1998, 2, 159-169.
19. (d) Yagai, S.; Miyatake, T.; Tamiaki, H. J. Photochem. Photobiol. B 1999, 52, 74-85.
20. (e) Tamiaki, H.; Kubo, M.; Oba, T. Tetrahedron 2000, 56, 6245-6257.
21. (f) Yagai, S.; Miyatake, T.; Shimono, Y.; Tamiaki, H. Photochem. Photobiol. 2001, 73, 153-163.
22. (g) Yagai, S.; Miyatake, T.; Tamiaki, H. J. Org. Chem. 2002, 67, 49-58.
23. (h) Tamiaki, H.; Amakawa, M.; Holzwarth, A. R.; Schaffner, K. Photosynth. Res. 2002, 71, 59-67.
24. (i) Tamiaki, H.; Kimura, S.; Kimura, T. Tetrahedron 2003, 59, 7423-7435.
25. (j) Tamiaki, H.; Omoda, M.; Saga, Y.; Morishita, H. Tetrahedron 2003, 59, 4337-4350.
26. (k) Sasaki, S.; Omoda, M.; Tamiaki, H. J. Photochem. Photobiol. A 2004, 162, 307-315.
27. (l) Miyatake, T.; Tamiaki, H.; Fujiwara, M.; Matsushita, T. Bioorg. Med. Chem. 2004, 12, 2173-2178.
28. (m) Sasaki, S.; Tamiaki, H. Bull. Chem. Soc. Jpn. 2004, 77, 797-800.
29. (a) Tamiaki, H.; Miyatake, T.; Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 772-774.
30. (b) Miyatake, T.; Tamiaki, H.; Holzwarth, A. R.; Schaffner, K. Helv. Chim. Acta 1999, 82, 797-810.
31. (c) Prokhorenko, V. I.; Holzwarth, A. R.; Müller, M. G.; Schaffner, K.; Miyatake, T.; Tamiaki, H. J. Phys. Chem. B 2002, 106, 5761-5768.
32. (d) Saga, Y.; Akai, S.; Miyatake, T.; Tamiaki, H. Chem. Lett. 2004, 33, 544-545.
33. Kunieda, M.; Mizoguchi, T.; Tamiaki, H. Photochem. Photobiol. 2004, 79, 55-61.
34. Pandey, R. K.; Isaac, M.; MacDonald, I.; Medforth, C. J.; Senge, M. O.; Dougherty, T. J.; Smith, K. M. J. Org. Chem. 1997, 62, 1463-1472.
35. (a) Linnanto, J.; Korppi-Tommola, J. J. Phys. Chem. A 2001, 105, 3855-3866.
36. (b) Tamiaki, H.; Watanabe, T.; Kunieda, M. Res. Chem. Intermed. 2005, 31, in press.
37. The 8- or 7-epimeric separation of 3-formyl-7-oxo-6 or 8-oxo-7 was easily done by normal-phase HPLC (see Figure S1 in the Supporting Information), and reduction of the resulting 8- or 7-epimerically pure sample gave the corresponding 8-epimerically pure 1-f1 and 1-f2, or 7-epimerically pure 2-f1 and 2-f2: f1 and f2 mean the first and second elutions on the HPLC separation. The self-aggregations of separated 1-f1 and 1-f2 had almost the same spectra except for time-dependent CD signals: the CD spectra were different just after preparation of the solution but became the same after standing for 1 day (see Figure S2A,B). Similar results were obtained for 2-f1 and 2-f2 (see Figure S2C,D). In this paper we focused on the difference between 7-oxo-1 and 8-oxo-2, and used their epimeric mixtures to compare the optical properties of the regioisomers.
38. (a) Amakawa, M.; Tamiaki, H. Bioorg. Med. Chem. 1999, 7, 1141-1144.
39. (b) Morishita, H.; Tamiaki, H. Bioorg. Med. Chem. 2003, 11, 4049-4057.
40. -1 of self-aggregated 1/2 was affected by the situation of the dialkyl group, not by the size of the alkyl substituents.