Synthesis and optical properties of bacteriochlorophyll-a derivatives having various C3 substituents on the bacteriochlorin π-system

Journal of Organic Chemistry

Volumn 71, Issue 7, 2006, Pages 2648-2654

  Sasaki, Shin Ichi ^a   Tamiaki, Hitoshi ^a  

^a RITSUMEIKAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MONOMERIC STATES; SUBSTITUENTS;

ABSORPTION; BACTERIA; CHLORINE; OPTICAL PROPERTIES; ORGANIC COMPOUNDS; ORGANIC SOLVENTS; OXIDATION; SYNTHESIS (CHEMICAL); ZINC COMPOUNDS;

CHLOROPHYLL;

BACTERIOCHLORIN; BACTERIOCHLOROPHYLL A; CYCLOHEXANE; METHYL GROUP; ORGANIC SOLVENT; PHEOPHORBIDE; ZINC COMPLEX;

ABSORPTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CIRCULAR DICHROISM; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; RHODOBACTER SPHAEROIDES; SYNTHESIS;

BACTERIOCHLOROPHYLL A; MOLECULAR CONFORMATION; OPTICS; OPTICS AND PHOTONICS; OXIDATION-REDUCTION; PORPHYRINS; STEREOISOMERISM;

EID: 33645531335     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0523969     Document Type: Article

References (39)

1. (a) Light-Harvesting Antennas in Photosynthesis; Green, B. R., Parson, W. W., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2003.
2. (b) Blankenship, R. E. In Molecular Mechanisms of Photosynthesis; Blackwell Science: London, UK, 2002.
3. Cogdell, R. J.; Gardiner, A. T.; Roszak, A. W.; Law, C. J.; Soughall, J.; Isaacs, N. W. Photosynth. Res. 2004, 81, 207-214.
4. Kunieda, M.; Mizoguchi, T.; Tamiaki, H. Photochem. Photobiol. 2004, 79, 55-61.
5. Linnanto, J.; Korppi-Tommola, J. J. Comput. Chem. 2004, 25, 123-137.
6. (a) Pandey, R. K.; Zheng, G. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 6, pp 157-230.
7. (b) Chen, Y.; Li, G.; Pandey, R. K. Curr. Org. Chem. 2004, 8, 1105-1134.
8. (a) Hartwich, G.; Fiedor, L.; Simonin, I.; Cmiel, E.; Schafer, W.; Noy, D.; Scherz, A.; Scheer, H. J. Am. Chem. Soc. 1998, 122, 3675-3683.
9. (b) Fukuzumi, S.; Ohkubo, K.; Chen, Y. H.; Pandey, R. K.; Zhan, R. Q.; Shao, J. G.; Kadish, K. M. J. Phys. Chem. A 2002, 106, 5105-5113.
10. (c) Mironov, A. F. M.; Grin, M. A.; Tsiprovskiy, A. G.; Vadim, V. K.; Karmakova, T. A.; Plyutinskaya, A. D.; Yakubovskaya, R. I. J. Porphyrins Phthalocyanines 2003, 7, 725-730.
11. (d) Chen, Y.; Sumlin, A.; Morgan, J.; Gryshuk, A.; Oseroff, A.; Henderson, B. W.; Dougherty, T. J.; Pandey, R. K. J. Med. Chem. 2004, 47, 4814-4817.
12. (e) Kim, H.-J.; Lindsey, J. S. J. Org. Chem. 2005, 70, 5475-5486.
13. (f) Brandis, A.; Mazor, O.; Neumark, E.; Rosenbach-Belkin, V.; Salomon, Y.; Scherz, A. Photochem. Photobiol. 2005, 8l, 983-993.
14. (a) Kunieda, M.; Mizoguchi, T.; Tamiaki, H. Tetrahedron 2004, 60, 11349-11357.
15. (b) Chen, Y.; Sumlin, A.; Morgan, J.; Gryshuk, A.; Oseroff, A.; Henderson, B. W.; Dougherty, T. J.; Pandey, R. K. J. Med. Chem. 2004, 47, 4814-4817.
16. (c) Mironov, A. F.; Grin, M. A.; Tsiprovskii, A. G.; Titeev, R. A.; Nizhnik, E. A.; Lonin, I. S. Mendeleev Commun. 2004, 204-207.
17. (d) Kunieda, M.; Tamiaki, H. J. Org. Chem. 2005, 70, 820-828.
18. Tamiaki, H.; Kouraba, M.; Takeda, K.; Kondo, S.; Tanikaga, R. Tetrahedron: Asymmetry 1998, 9, 2101-2111.
19. Struck, A.; Cmiel, E.; Katheder, I.; Schäfer, W.; Scheer, H. Biochim. Biophys. Acta 1992, 1101, 321-328.
20. Tamiaki, H.; Amakawa, M.; Shimono, Y.; Tanikaga, R.; Holzwarth, A. R.; Schaffner, K. Photochem. Photobiol. 1996, 63, 92-93.
21. About 0.1 mM solution of pure 4 in acetone/1,2-dichloroethane (1:9) was stored in the dark at room temperature under air, and analyzed by HPLC. Neither oxidation to chlorin 5 nor decomposition was observed for 10 days.
22. Tamiaki, H.; Watanabe, T.; Miyatake, T. J. Porphyrins Phthalocyanines 1999, 3, 45-52.
23. Osuka, A.; Wada, Y.; Shinoda, S. Tetrahedron 1996, 52, 4311-4326.
24. 2. The resulting oligo(2-methyl-2-butene) made it difficult to purify 7 from the reaction mixture. The relatively low yield is ascribed in part to the adsorption during the repeated column chromatography.
25. Tamiaki, H.; Yagai, S.; Miyatake, T. Bioorg. Med. Chem. 1998, 6, 2171-2178.
26. Tamiaki, H.; Kouraba, M. Tetrahedron 1997, 53, 10677-10688.
27. (a) Tamiaki, H. Coord. Chem. Rev. 1996, 148, 183-197.
28. (b) Olson, J. M. Photochem. Photobiol. 1998, 67, 61-75.
29. (c) Frigaard, N.-U.; Chew, A. G. M.; Li, H.; Maresca, J. A.; Bryant, D. A. Photosynth. Res. 2003, 78, 93-117.
30. (d) Miyatake, T.; Tamiaki, H. J. Photochem. Photobiol. C: Photochem. Rev. 2005, 6, 89-107.
31. (e) Balaban, T. S. Acc. Chem. Res. 2005, 38, 612-623.
32. Tamiaki, H.; Kitamoto, H.; Watanabe, T.; Shibata, R. Photochem. Photobiol. 2005, 81, 170-176.
33. Tamiaki, H.; Kubota, T.; Tanikaga, R. Chem. Lett. 1996, 639-640.
34. (a) Tamiaki, H.; Kubo, M.; Oba, T. Tetrahedron 2000, 56, 6245-6257.
35. (b) Yagai, S.; Miyatake, T.; Shimono, Y.; Tamiaki, H. Photochem. Photobiol. 2001, 73, 153-163.
36. (a) Parson, W. W.; Warshel, A. J. Am. Chem. Soc. 1987, 109, 6152-6163.
37. (b) Gudowska-Nowak, E.; Newton, M. D.; Fajer, J. J. Phys. Chem. 1990, 94, 5795-5801.
38. (c) Cogdell, R. J.; Howard, T. D.; Isaacs, N. W.; McLuskey, K.; Gardiner, A. T. Photosyn. Res. 2002, 74, 135-141.
39. Tamiaki, H.; Takeuchi, S.; Tsuzuki, S.; Miyatake, T.; Tanikaga, R. Tetrahedron 1998, 54, 6699-6718.