Diastereoselective Self-aggregation of Synthetic 3-(1-Hydroxyethyl)-bacteriopyrochlophyll-a as a Novel Photosynthetic Antenna Model Absorbing Near the Infrared Region

Photochemistry and Photobiology

Volumn 79, Issue 1, 2004, Pages 55-61

  Kunieda, Michio ^a   Mizoguchi, Tadashi ^a   Tamiaki, Hitoshi ^a  

^a RITSUMEIKAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 DEACETYL 3 (1 HYDROXYETHYL)BACTERIOPYROCHLOROPHYLL A; CHLOROPHYLL A; CYCLOHEXANE; DICHLOROMETHANE; UNCLASSIFIED DRUG;

ANTENNA; ARTICLE; CHEMICAL STRUCTURE; DERIVATIZATION; DIASTEREOISOMER; EPIMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGHT ABSORPTION; MODEL; NEAR INFRARED SPECTROSCOPY; NONHUMAN; PHOTOSYNTHESIS; PHOTOTROPHIC BACTERIUM; STEREOCHEMISTRY; SUPRAMOLECULAR CHEMISTRY;

BACTERIOCHLOROPHYLLS; INFRARED RAYS; MODELS, BIOLOGICAL; MODELS, MOLECULAR; PHOTOSYNTHESIS;

PHOTOBACTERIA; PROTEOBACTERIA;

EID: 0842291518     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2004)79<55:DSOSHA>2.0.CO;2     Document Type: Article

References (51)

1. Zuber, H. and R. J. Cogdell (1995) Structure and organization of purple bacterial antenna complexes. In Anoxygenic Photosynthetic Bacteria (Edited by R. E. Blankenship, M. T. Madigan and C. E. Bauer), pp. 315-348. Kluwer Academic Publishers, Dordrecht.
2. Loach, P. A. and P. S. Parkes-Loach (1995) Structure-function relationships in core light-harvesting complexes (LHI) as determined by characterization of the structural subunit and by reconstitution experiments. In Anoxygenic Photosynthetic Bacteria (Edited by R. E. Blankenship, M. T. Madigan and C. E. Bauer), pp. 437-471. Kluwer Academic Publishers, Dordrecht.
3. Olson, J. M. (1998) Chlorophyll organization and function in green photosynthetic bacteria. Photochem. Photobiol. 67, 61-75.
4. Blankenship, R. E. and K. Matsuura (2003) Antenna complexes from green photosynthetic bacteria. In Light-Harvesting Antennas in Photosynthesis (Edited by B. R. Green and W. W. Parson). 195-217 Kluwer Academic Publishers, Dordrecht.
5. Tamiaki, H. (1996) Supramolecular structure in extramembraneous antennae of green photosynthetic bacteria. Cood. Chem. Rev. 148, 183-197.
6. Tamiaki, H., A. R. Holzwarth and K. Schaffner (1992) A synthetic zinc chlorin aggregates as a model for the supramolecular antenna complexes in the chlorosomes of green bacteria. J. Photochem. Photobiol. B: Biol. 15, 355-360.
7. Matsuura, K., M. Hitota, K. Shimada and M. Mimuro (1993) Spectral forms and orientation of bacteriochlorophylls c and a in chlorosomes of the green photosynthetic bacterium Chloroflexus aurantiacus. Photochem. Photobiol. 57, 92-97.
8. 13C NMR. Photosynth. Res. 41, 211-223.
9. Holzwarth, A. R. and K. Schaffner (1994) On the structure of bacteriochlorophyll molecular aggregates in the chlorosomes of green bacteria. A molecular modelling study. Photosynth. Res. 41, 225-233.
10. 1H NOE correlations. Photochem. Photobiol. 67, 239-248.
11. Van Rossum, B.-J., D. B. Steensgaard, F. M. Mulder, G. J. Boender, K. Schaffner, A. R. Holzwarth and H. J. M. de Groot (2001) A refined model of the chlorosomal antennae of the green bacterium Chlorobium tepidum from proton chemical shift constraints obtained with high-field 2-D and 3-D MAS NMR dipolar correlation spectroscopy. Biochemistry 40, 1587-1595.
12. Psěnčik, J., Y.-Z. Ma, J. B. Arellano, J. Hála and T. Gillbro (2003) Excitation energy transfer dynamics and excited-state structure in chlorosomes of Chlorobium phaeobacteroides. Biophys. J. 84, 1161-1179.
13. 1-epimeric zinc methyl bacteriopyropheophorbides-d in apolar solvents. Chem. Lett. 401-402.
14. Mizoguchi, T., K. Hara, H. Nagae and Y. Koyama (2000) Structural transformation among the aggregate forms of bacteriochlorophyll c as determined by electronic-absorption and NMR spectroscopies: Dependence on the stereoisomeric configuration and on the bulkiness of the 8-C side chain. Photochem. Photobiol. 71, 596-609.
15. 1-S-BChl e is essential for the formation of chlorosome-like aggregates. J. Phys. Chem. B 104, 10379-10386.
16. 1-hydroxy group: visible spectroscopic and molecular modeling studies. Photochem. Photobiol. 73, 153-163.
17. Causgrove, T. P., D. C. Brune and R. E. Blankenship (1992) Förster energy transfer in chlorosomes of green photosynthetic bacteria. J. Photochem. Photobiol. B: Biol. 15, 171-179.
18. Smith, K. M., L. A. Kehres and J. Fajer (1983) Aggregation of the bacteriochlorophylls c, d, and e. Models for the antenna chlorophylls of green and brown photosynthetic bacteria. J. Am. Chem. Soc. 105, 1387-1389.
19. s, aggregation. J. Phys. Chem. 99, 1357-1365.
20. 1 epimers by light intensity. Photochem. Photobiol. 71, 567-573.
21. Bystrova, M. I., I. N. Mal'gosheva and A. A. Krasnovskii (1979) Study of molecular mechanism of self-assembly of aggregated forms of bacteriochlorophyll c. Mol. Biol. 13, 440-451.
22. Brune, D. C., T. Nozawa and R. E. Blankenship (1987) Antenna organization in green photosynthetic bacteria. 1. Oligomeric bacteriochlorophyll c as a model for the 740 nm-absorbing bacteriochlorophyll c in Chloroflexus aurantiacus chlorosomes. Biochemistry 26, 8644-8652.
23. F molecules in nonpolar solvents. Analysis of the kinetics. J. Phys. Chem. B 104, 1362-1372.
24. Tamiaki, H., M. Amakawa, Y. Shimono, R. Tanikaga, A. R. Holzwarth and K. Schaffner (1996) Synthetic zinc and magnesium chlorin aggregates as models for supramolecular antenna complexes in chlorosomes of photosynthetic bacteria. Photochem. Photobiol. 63, 92-99.
25. Tamiaki, H., S. Miyata, Y. Kureishi and R. Tanikaga (1996) Aggregation of synthetic zinc chlorins with several esterified alkyl chains as models of bacteriochlorophyll-c homologs. Tetrahedron 52, 12421-12432.
26. Kureishi, Y. and H. Tamiaki (1998) Synthesis and self-aggregation of zinc 20-halogeno-chlorins as a model for bacteriochlorophylls c/d. J. Porphyrins Phthalocyanines 2, 159-169.
27. Miyatake, T., H. Tamiaki, A. R. Holzwarth and K. Schaffner (1999) Artificial light-harvesting antennae: singlet excitation energy transfer from zinc chlorin aggregate to bacteriochlorin in homogeneous hexane solution. Photochem. Photobiol. 69, 448-456.
28. Tamiaki, H., M. Kubo and T. Oba (2000) Synthesis and self-assembly of zinc methyl bacteriopheophorbide-f and its homolog. Tetrahedron 56, 6245-6257.
29. Tamiaki, H., M. Amakawa, A. R. Holzwarth and K. Schaffner (2002) Aggregation of synthetic metallochlorins in hexane. A model of chlorosomal bacteriochlorophyll self-assemblies in green bacteria. Photosynth. Res. 71, 59-67.
30. Tamiaki, H., M. Omoda, Y. Saga and H. Morishita (2003) Synthesis of homologously pure bacteriochlorophyll-e and fanalogues from BChls-c/d via transformation of the 7-methyl to formyl group and self-aggregation of synthetic zinc methyl bacteriopheophorbides-c/d/e/f in non-polar organic solvent. Tetrahedron 59, 4337-4350.
31. Tamiaki, H., T. Kubota and R. Tanikaga (1996) Aggregation of synthetic zinc complexes of cyclotetrapyrroles. Chem. Lett. 639-640.
32. Tamiaki, H., M. Kouraba, K. Takeda, S. Kondo and R. Tanikaga (1998) Asymmetric synthesis of methyl bacteriopheophorbide-d and analogues by stereoselective reduction of the 3-acetyl to the 3-(1-hydroxyethyl) group. Tetrahedron Asymmetry, 9, 2101-2111.
33. 2. Biochim. Biophys. Acta 1101, 321-328.
34. Tamiaki, H., S. Takeuchi, S. Tsudzuki, T. Miyatake and R. Tanikaga (1998) Self-aggregation of synthetic zinc chlorins with chiral 1-hydroxyethyl group as a model for in vivo epimeric bacteriochlorophyll-c and d aggregates. Tetrahedron 54, 6699-6718.
35. Smith, K. M., G. W. Craig, L. A. Kehres and N. Pfennig (1983) Reversed-phase high-performance liquid chromatography and structural assignments of the bacteriochlorophylls-c. J. Chromatogr. 281, 209-223.
36. Smith, K. M. and D. A. Goff (1985) Bacteriochlorophylls-d from Chlorobium vibrioforme: chromatographic separations and structural assignments of the methyl bacteriopheophorbides. J. Chem. Soc. Perkin Trans. 1 1099-1113.
37. 1-position. Photochem. Photobiol. 74, 72-80.
38. Tamiaki, H., A. R. Holzwarth and K. Schaffner (1994) Dimerization of synthetic zinc aminochlorins in non-polar organic solvents. Photosynth. Res. 41, 245-251.
39. Yagai, S., T. Miyatake and H. Tamiaki (2002) Regio- and stereoisomeric control of the aggregation of zinc-chlorins possessing inverted interactive hydroxyl and carbonyl groups. J. Org. Chem. 67, 49-58.
40. Smith, K. M. (2003) Chlorosome chlorophylls (bacteriochlorophylls c, d, and e): structures, partial syntheses, and biosynthetic proposal. In The Polphyrin Handbook, Vol. 13 (Edited by K. M. Kadish, K. M. Smith and R. Guilard), pp. 157-182. Academic Press, San Diego.
41. Nozawa, T., K. Ohmoto, N. Takeshita, Y. Morishita, M. Osawa and M. T. Madigan (1992) Substituent effects on the aggregation of bacteriochlorophyll d homologues purified from Chlorobium limicola. Bull. Chem. Soc. Jpn. 65, 3493-3494.
42. Mizoguchi, T., Y. Saga and H. Tamiaki (2002) Isolation and structure determination of a complete set of bacteriochlorophyll-d homologs and epimers from a green sulfur bacterium Chlorobium vibrioforme and their aggregation properties in hydrophobic solvents. Photochem. Photobiol. Sci. 1, 780-787.
43. Miyatake, T., T. Oba and H. Tamiaki (2001) Pure and scrambled self-aggregates prepared with zinc analogues of bacteriochlorophylls c and d. ChemBioChem 2, 335-342.
44. Oba, T. and H. Tamiaki (2001) Effect of C-7-substituent on self-assembly of chlorosomal chlorophylls. Supramol. Chem. 12, 369-378.
45. Meadows, K. A., P. S. Parkes-Loach, J. W. Kehoe and P. A. Loach (1998) Reconstitution of core light-harvesting complexes of photosynthetic bacteria using chemically synthesized polypeptides. 1. Minimal requirements for subunit formation. Biochemistry 37, 3411-3417.
46. Karrasch, S., P. A. Bullough and R. Ghosh (1995) 8.5 Å projection structure of the light-harvesting complex I from Rhodospirillum rubrum reveals a ring composed of 16 subunits. EMBO J. 14, 631-638.
47. Walz, T. and R. Ghosh (1997) Two-dimensional crystallization of the light-harvesting I-reaction centre photounit from Rhodospirillum rubrum. J. Mol. Biol. 265, 107-111.
48. Jungas, C., J.-L. Ranck, J.-L. Rigaud, P. Joliot and A. Verméglio (1999) Supramolecular organization of the photosynthetic apparatus of Rhodobacter sphaeroides. EMBO J. 18, 534-542.
49. Loach, P. A. (2000) Supramolecular complexes in photosynthetic bacteria. Proc. Natl. Acad. Sci. USA 97, 5016-5018.
50. Frese, R. N., J. D. Olsen, R. Branvall, W. H. J. Westerhuis, C. N. Hunter and R. van Grondelle (2000) The long-range supraorganization of the bacterial photosynthetic unit: a key role for PufX. Proc. Natl. Acad. Sci. USA 97, 5197-5202.
51. Blankenship, R. E., J. M. Olson and M. Miller (1995) Antenna complexes from green photosynthetic bacteria. In Anoxygenic Photosynthetic Bacteria (Edited by R. E. Blankenship, M. T. Madigan and C. E. Bauer), pp. 399-435. Kluwer Academic Publishers, Dordrecht.