Synthesis and structural properties of porphyrin analogues of bacteriochlorophyll c

Tetrahedron

Volumn 63, Issue 51, 2007, Pages 12629-12638

  Ptaszek, Marcin ^a   Yao, Zhen ^a   Savithri, Dhanalekshmi ^a   Boyle, Paul D ^a   Lindsey, Jonathan S ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

Crystal; Light harvesting; Photosynthesis; Porphyrin; Self assembly

Indexed keywords

BACTERIOCHLOROPHYLL; BACTERIOCHLOROPHYLL C; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG; ZINC 15 (ETHOXYCARBONYL) 3 HYDROXYMETHYL 10,20 DI 4 TOLYLPORPHYRIN;

ARTICLE; BROMINATION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; PHOTOSYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 35748985881     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.10.023     Document Type: Article

References (76)

1. Green B.R., Anderson J.M., and Parson W.W. In: Green B.R., and Parson W.W. (Eds). Light-Harvesting Antennas in Photosynthesis (2003), Kluwer Academic, The Netherlands 1-28
2. Blankenship R.E., Olson J.M., and Miller M. In: Blankenship R.E., Madigan M.T., and Bauer C.E. (Eds). Anoxygenic Photosynthetic Bacteria (1995), Kluwer Academic, The Netherlands 399-435
3. Scheer H. In: Grimm B., Porra R.J., Rüdiger W., and Scheer H. (Eds). Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications (2006), Kluwer Academic, The Netherlands 1-26
4. Tamiaki H. Coord. Chem. Rev. 148 (1996) 183-197
5. Tamiaki H., Holzwarth A.R., and Schaffner K. J. Photochem. Photobiol., B: Biol. 15 (1992) 355-360
6. Tamiaki H., Takeuchi S., Tanikaga R., Balaban S.T., Holzwarth A.R., and Schaffner K. Chem. Lett. (1994) 401-402
7. Tamiaki H., Holzwarth A.R., and Schaffner K. Photosynth. Res. 41 (1994) 245-251
8. Tamiaki H., Miyata S., Kureishi Y., and Tanikaga R. Tetrahedron 52 (1996) 12421-12432
9. Tamiaki H., Kubota T., and Tanikaga R. Chem. Lett. 8 (1996) 639-640
10. Tamiaki H., Amakawa M., Shimono Y., Tanikaga R., Holzwarth A.R., and Schaffner K. Photochem. Photobiol. 63 (1996) 92-99
11. Tamiaki H., Miyatake T., Tanikaga R., Holzwarth A.R., and Schaffner K. Angew. Chem., Int. Ed. 35 (1996) 772-774
12. Tamiaki H., Miyatake T., and Tanikaga R. Tetrahedron Lett. 38 (1997) 267-270
13. Tamiaki H., and Kouraba M. Tetrahedron 53 (1997) 10677-10688
14. Balaban T.S., Tamiaki H., Holzwarth A.R., and Schaffner K. J. Phys. Chem. B 101 (1997) 3424-3431
15. Oba T., Furukawa H., Wang Z.-Y., Nozawa T., Mimuro M., Tamiaki H., and Watanabe T. J. Phys. Chem. B 102 (1998) 7882-7889
16. Tamiaki H., Takeuchi S., Tsudzuki S., Miyatake T., and Tanikaga R. Tetrahedron 54 (1998) 6699-6718
17. Kureishi Y., and Tamiaki H. J. Porphyrins Phthalocyanines 2 (1998) 159-169
18. Oba T., and Tamiaki H. Photochem. Photobiol. 67 (1998) 295-303
19. Oba, T.; Tamiaki, H. In: Photosynthesis: Mechanisms and Effects, Proceedings of the International Congress on Photosynthesis, 11th, Budapest, Aug. 17-22, 1998; Garab, G., Ed.; Kluwer Academic: Netherlands, 1998; Vol. 1, pp 465-468.
20. Miyatake, T.; Tamiaki, H.; Holzwarth, A.R.; Schaffner, K. In: Photosynthesis: Mechanisms and Effects, Proceedings of the International Congress on Photosynthesis, 11th, Budapest, Aug. 17-22, 1998; Garab, G., Ed.; Kluwer Academic: Netherlands, 1998; Vol. 1, pp 133-136
21. Yagai S., Miyatake T., and Tamiaki H. J. Photochem. Photobiol., B: Biol. 52 (1999) 74-85
22. Oba T., and Tamiaki H. Photosynth. Res. 61 (1999) 23-31
23. Miyatake T., Tamiaki H., Holzwarth A.R., and Schaffner K. Photochem. Photobiol. 69 (1999) 448-456
24. Tamiaki H., Kubo M., and Oba T. Tetrahedron 56 (2000) 6245-6257
25. Yagai S., Miyatake T., Shimono Y., and Tamiaki H. Photochem. Photobiol. 73 (2001) 153-163
26. Yagai S., and Tamiaki H. J. Chem. Soc., Perkin Trans. 1 (2001) 3135-3144
27. Miyatake T., Oba T., and Tamiaki H. ChemBioChem 2 (2001) 335-342
28. Yagai S., Miyatake T., and Tamiaki H. J. Org. Chem. 67 (2002) 49-58
29. Tamiaki H., Amakawa M., Holzwarth A.R., and Schaffner K. Photosynth. Res. 71 (2002) 59-67
30. Prokhorenko V.I., Holzwarth A.R., Müller M.G., Schaffner K., Miyatake T., and Tamiaki H. J. Phys. Chem. B 106 (2002) 5761-5768
31. Miyatake T., Tamiaki H., Shinoda H., Fujiwara M., and Matsushita T. Tetrahedron (2002) 9989-10000
32. Tamiaki H., Omoda M., Saga Y., and Morishita H. Tetrahedron 59 (2003) 4337-4350
33. Tamiaki H., Kimura S., and Kimura T. Tetrahedron 59 (2003) 7423-7435
34. Sasaki S.-i., Omoda M., and Tamiaki H. J. Photochem. Photobiol., A: Chem. 162 (2004) 307-315
35. Sasaki S.-i., and Tamiaki H. Bull. Chem. Soc. Jpn. 77 (2004) 797-800
36. Kunieda M., Mizoguchi K., and Tamiaki H. Photochem. Photobiol. 79 (2004) 55-61
37. de Boer I., Matysik J., Erkelens K., Sasaki S.-i., Miyatake T., Yagai S., Tamiaki H., Holzwarth A.R., and de Groot H.J.M. J. Phys. Chem. B 108 (2004) 16556-16566
38. Tamiaki H., Kitamoto H., Nishikawa A., Hibino T., and Shibata R. Bioorg. Med. Chem. 12 (2004) 1657-1666
39. Kunieda M., and Tamiaki H. Eur. J. Org. Chem. (2006) 2352-2361
40. Miyatake T., Tanigawa S., Kato S., and Tamiaki H. Tetrahedron Lett. 48 (2007) 2251-2254
41. Kunieda M., and Tamiaki H. J. Org. Chem. 72 (2007) 2443-2451
42. Balaban T.S., Eichhöfer A., and Lehn J.-M. Eur. J. Org. Chem. (2000) 4047-4057
43. Balaban T.S., Bhise A.D., Fischer M., Linke-Schaetzel M., Roussel C., and Vanthuyne N. Angew. Chem., Int. Ed. 42 (2003) 2140-2144
44. Balaban T.S., Linke-Schaetzel M., Bhise A.D., Vanthuyne N., and Roussel C. Eur. J. Org. Chem. (2004) 3919-3930
45. Balaban T.S., Linke-Schaetzel M., Bhise A.D., Vanthuyne N., Roussel C., Anson C.E., Buth G., Eichhöfer A., Foster K., Garab G., Gliemann H., Goddard R., Javorfi T., Powell A.K., Rösner H., and Schimmel T. Chem.-Eur. J. 11 (2005) 2267-2275
46. Balaban T.S., Tamiaki H., and Holzwarth A.R. Top. Curr. Chem. 258 (2005) 1-38
47. Balaban T.S. Acc. Chem. Res. 38 (2005) 612-623
48. Miyatake T., and Tamiaki H. J. Photochem. Photobiol., C: Photochem. Rev. 6 (2005) 89-107
49. Tamiaki H., Shibata R., and Mizoguchi T. Photochem. Photobiol. 83 (2007) 152-162
50. Kobuke Y. Struct. Bonding 121 (2006) 49-104
51. Yao Z., Bhaumik J., Savithri D., Ptaszek M., Rodriguez P., and Lindsey J.S. Tetrahedron 63 (2007) 10657-10670
52. Kamogawa H., Nakata T., and Komatsu S. Bull. Chem. Soc. Jpn. 64 (1991) 2300-2302
53. Vicente M.G.H. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook Vol. 1 (2000), Academic, San Diego, CA 149-199
54. Jaquinod L. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook Vol. 1 (2000), Academic, San Diego, CA 201-237
55. Balasubramanian T., and Lindsey J.S. Tetrahedron 55 (1999) 6771-6784
56. Balasubramanian T., Strachan J.-P., Boyle P.D., and Lindsey S.J. J. Org. Chem. 65 (2000) 7919-7929
57. Liu Z., Yasseri A.A., Loewe R.S., Lysenko A.B., Malinovskii V.L., Zhao Q., Surthi S., Li Q., Misra V., Lindsey J.S., and Bocian D.F. J. Org. Chem. 69 (2004) 5568-5577
58. Tamaru S.-I., Yu L., Youngblood W.J., Muthukumaran K., Taniguchi M., and Lindsey J.S. J. Org. Chem. 69 (2004) 765-777
59. Lee C.-H., Li F., Iwamoto K., Dadok J., Bothner-By A.A., and Lindsey J.S. Tetrahedron 51 (1995) 11645-11672
60. Rao P.D., Dhanalekshmi S., Littler B.J., and Lindsey J.S. J. Org. Chem. 65 (2000) 7323-7344
61. Geier III G.R., Callinan J.B., Rao P.D., and Lindsey J.S. J. Porphyrins Phthalocyanines 5 (2001) 810-823
62. Trova M.P., Gauuan P.J.F., Pechulis A.D., Bubb S.M., Bocckino S.B., Crapo J.D., and Day B.J. Bioorg. Med. Chem. 11 (2003) 2695-2707
63. Srinivasan N., Haney C.A., Lindsey J.S., Zhang W., and Chait B.T. J. Porphyrins Phthalocyanines 3 (1999) 283-291
64. Kosugi M., Sumiya T., Ogata T., Sano H., and Migita T. Chem. Lett. (1984) 1225-1226
65. Kosugi M., Sumiya T., Ohhashi K., Sano H., and Migita T. Chem. Lett. (1985) 997-998
66. Danheiser R.L., Romines K.R., Koyama H., Gee S.K., Johnson C.R., and Medich J.R. Org. Synth. 71 (1993) 133-139
67. Åhman J., and Somfai P. Synth. Commun. 24 (1994) 1117-1120
68. Muthiah C., Bhaumik J., and Lindsey J.S. J. Org. Chem. 72 (2007) 5839-5842
69. Scheidt W.R., and Lee Y.J. In: Buchler J.W. (Ed). Structure and Bonding Vol. 64 (1987), Springer, Berlin 1-70
70. Senge M.O. In: Kadish K.M., Smith K.M., and Guilard R. (Eds). The Porphyrin Handbook Vol. 10 (2000), Academic, San Diego, CA 1-218
71. Desiraju G.R. Acc. Chem. Res. 24 (1991) 290-296
72. Bruker-Nonius. SAINT+ version 7.07B (2004), Bruker-Nonius, Madison, WI
73. Bruker-Nonius. SADABS version 2.10 (2004), Bruker-Nonius, Madison, WI
74. Altomare A., Cascarano G., Giacovazzo C., Guagliardi A., Burla M.C., Polidori G., and Camalli M. J. Appl. Crystallogr. 27 (1994) 435
75. Bruker-AXS, XL, SHELXTL version 6.12, UNIX (2001), Bruker-Nonius, Madison, WI
76. Gabe E.J., Le Page Y., Charland J.-P., Lee F.L., and White P.S. J. Appl. Crystallogr. 22 (1989) 384-387