Effects of peripheral substituents on diastereoselectivity of the fifth ligand-binding to chlorophylls, and nomenclature of the asymmetric axial coordination sites

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 20, 2005, Pages 5733-5739

  Oba, Toru ^a,c   Tamiaki, Hitoshi ^b  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b RITSUMEIKAN UNIVERSITY   (Japan)

^c UTSUNOMIYA UNIVERSITY   (Japan)

Author keywords

Bacteriochlorophyll; Chirality; Chlorophyll; Coordination; Diastereomer; Epimer

Indexed keywords

BACTERIOCHLOROPHYLL; CARBONYL DERIVATIVE; CHLOROPHYLL; METAL;

ANALYTIC METHOD; ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CRYSTALLOGRAPHY; DIASTEREOISOMER; LIGAND BINDING; STATISTICAL SIGNIFICANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

BINDING SITES; CHLOROPHYLL; LIGANDS; MOLECULAR STRUCTURE; STEREOISOMERISM; TERMINOLOGY;

EID: 24344465706     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.06.016     Document Type: Article

References (40)

1. T. Oba, and H. Tamiaki Photosynth. Res. 74 2002 1
2. T.S. Balaban, P. Fromme, A.R. Holzwarth, N. Krauß, and V.I. Prokhorenko Biochim. Biophys. Acta 1556 2002 197
3. T.S. Balaban FEBS Lett. 545 2003 97
4. A. Ben-Shem, F. Frolow, and N. Nelson Nature 426 2003 630
5. N. Krauß, M.D. Schubert, O. Klukas, P. Fromme, H.T. Witt, and W. Saenger Nat. Struct. Biol. 3 1996 965
6. D. Stroebel, Y. Choquet, J.-L. Popot, and D. Picot Nature 426 2003 413
7. G. Kurisu, H. Zhang, J.L. Smith, and W.A. Cramer Science 302 2003 1009
8. A. Zouni, H.T. Witt, J. Kern, P. Fromme, N. Krauß, W. Saenger, and P. Orth Nature 409 2001 739
9. S. Vasilév, P. Orth, A. Zouni, T.G. Owens, and D. Bruce Proc. Natl. Acad. Sci. U.S.A. 98 2001 8602
10. N. Kamiya, and J.-R. Shen Proc. Natl. Acad. Sci. U.S.A. 100 2003 98
11. K.N. Ferreira, T.M. Iverson, K. Maghlaouli, J. Barber, and S. Iwata Science 303 2004 1831
12. J. Biesiadka, B. Loll, J. Kern, K.D. Irrgang, and A. Zouni Phys. Chem. Chem. Phys. 6 2004 4733
13. W. Kühlbrandt, D.N. Wang, and Y. Fujiyoshi Nature 367 1994 614
14. Z. Liu, H. Yan, K. Wang, T. Kuang, J. Zhang, L. Gui, X. An, and W. Chang Nature 428 2004 287
15. T. Oba, and H. Tamiaki A. van der Est D. Bruce Photosynthesis: Fundamental Aspects to Global Perspectives 2005 Allen Press Lawrence, KS 886 888
16. H. Xu, D. Vavilin, and W. Vermaas Proc. Natl. Acad. Sci. U.S.A. 98 2001 14168
17. S. Satoh, M. Ikeuchi, M. Mimuro, and A. Tanaka J. Biol. Chem. 276 2001 4293
18. J. Duncan, T. Bibby, A. Tanaka, and J. Barber FEBS Lett. 541 2003 171
19. T. Miyashita, H. Ikemoto, N. Kurano, K. Adachi, M. Chihara, and S. Miyachi Nature 383 1996 402
20. T. Mizoguchi, H. Oh-oka, and H. Tamiaki Photochem. Photobiol. 81 2005 666
21. N. Wakao, N. Yokoi, N. Isoyama, A. Hiraishi, K. Shimada, M. Kobayashi, H. Kise, M. Iwaki, S. Itoh, S. Takaichi, and Y. Sakura Plant Cell Physiol. 37 1996 889
22. H. Furukawa, T. Oba, H. Tamiaki, and T. Watanabe Bull. Chem. Soc. Jpn. 73 2000 1341
23. H. Tamiaki, M. Amakawa, Y. Shimono, R. Tanikaga, A.R. Holzwarth, and K. Schaffner Photochem. Photobiol. 63 1996 92
24. T. Oba, and H. Tamiaki Photosynth. Res. 61 1999 23
25. H. Tamiaki, H. Kitamoto, T. Watanabe, and R. Shibata Photochem. Photobiol. 81 2005 170
26. J. Linnanto, and J. Korppi-Tommola J. Phys. Chem. A 108 2004 5872
27. P.H. Hynninen, and G. Sievers Z. Naturforsch. B 36 1981 1000
28. H. Mazaki, and T. Watanabe Bull. Chem. Soc. Jpn. 61 1988 2969
29. 2-(R/S)-Me: +0.5/-0.5 kcal/mol; C17-(R/S)-Me: +0.5/-0.5 kcal/mol; C18-(R/S)-Me: +0.1/-0.1 kcal/mol.
30. Our preliminary ab initio calculations (HF/3-21G) also showed that the 'back' type imidazole complex of Zn-MeChlid a was more stable than the 'face' one.
31. M.O. Senge, K. Ruhlandt-Senge, and K.M. Smith Z. Naturforsch. B 50 1995 139
32. N. Kosaka, and H. Tamiaki Eur. J. Org. Chem. 2004 2325
33. Recently, Balaban offered the same naming as ours (α/β = 'back'/'face'); see Balaban, T. S.; Tamiaki, H.; Holzwarth, A. R. In Supramolecular Dye Chemistry (Topics in Current Chemistry, vol. 258); Würthner, F., Ed.; Springer: Heidelberg, 2005; in press.
34. IUPAC rule 'Nomenclature of Corrinoids,' http://www.chem.qmul.ac.uk/ iupac/misc/B12.html
35. IUPAC rule 'Nomenclature of Tetrapyrroles,' http://www.chem.qmul.ac.uk/ iupac/tetrapyrrole/
36. For chlorin, phorbin, and corrin whose mother ring systems are asymmetric, the directions of the numbering are the same for trivial and systematic nomenclatures.
37. Nomenclature of Inorganic Chemistry, Recommendations 1990; Leigh, G. J., Ed.; Blackwell Scientific Publications: Oxford, UK, 1990
38. Yamasaki, K. Muki Kagaku Meimeiho, Tokyo Kagaku Dozin Co., Tokyo, 1993 (in Japanese).
39. M.F. Brown, B.R. Cook, and T.E. Sloan Inorg. Chem. 14 1975 1273
40. C, clockwise; A, anti-clockwise; TP, tetrapyrrole.