Total syntheses of sterically locked phycocyanobilin derivatives bearing a 15Z-anti or a 15E-anti CD-ring component

Bulletin of the Chemical Society of Japan

Volumn 83, Issue 11, 2010, Pages 1309-1322

  Nishiyama, Kaori ^a   Kamiya, Ayumi ^a   Hammam, Mostafa A S ^a   Kinoshita, Hideki ^a   Fujinami, Shuhei ^a   Ukaji, Yutaka ^a   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC CONDITIONS; COUPLING REACTION; DETOSYLATION; REGIOISOMERS; RING COMPONENTS; TOTAL SYNTHESIS;

STEREOCHEMISTRY;

CHROMOPHORES;

EID: 78649372107     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.20100168     Document Type: Article

References (48)

1. H. A. Borthwick, S. B. Hendricks, M. W. Parker, E. H. Toole, V. K. Toole, Proc. Natl. Acad. Sci. U.S.A. 1952, 38, 662;
2. W. L. Butler, K. H. Norris, H. W. Siegelman, S. B. Hendricks, Proc. Natl. Acad. Sci. U.S.A. 1959, 45, 1703.
3. K. C. Yeh, S. H. Wu, J. T. Murphy, J. C. Lagarias, Science 1997, 277, 1505;
4. T. Lamparter, F. Mittmann, W. Gärtner, T. Börner, E. Hartmann, J. Hughes, Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 11792;
5. S. J. Davis, A. V. Vener, R. D. Vierstra, Science 1999, 286, 2517.
6. S. H. Bhoo, S. J. Davis, J. Walker, B. Karniol, R. D. Vierstra, Nature 2001, 414, 776.
7. C. Starostzik, W. Marwan, FEBS Lett. 1995, 370, 146.
8. J. C. Lagarias, H. Rapoport, J. Am. Chem. Soc. 1980, 102, 4821;
9. H. Falk, The Chemistry of Linear Oligopyrroles and Bile Pigments, Springer Verlag, New York, 1989;
10. W. Rüdiger, F. Thümmler, Angew. Chem., Int. Ed. Engl. 1991, 30, 1216.
11. M. Furuya, P.-S. Song, in Assembly and Properties of Holophytochrome in Photomorphogenesis in Plants, 2nd ed., ed. by R. E. Kendrick, G. H. M. Kronenberg, Kluwer Academic Publishers, Dordrecht, The Netherlands, 1994, Chap. 4.3, pp. 105140;
12. M. Stanek, K. Grubmayr, Chem.-Eur. J. 1998, 4, 1653;
13. M. Stanek, K. Grubmayr, Chem.-Eur. J. 1998, 4, 1660;
14. T. Lamparter, FEBS Lett. 2004, 573, 1;
15. N. C. Rockwell, J. C. Lagarias, Plant Cell 2006, 18, 4;
16. N. C. Rockwell, Y.-S. Su, J. C. Lagarias, Annu. Rev. Plant Biol. 2006, 57, 837.
17. W. Rüdiger, F. Thümmler, in Photomorphogenesis in Plants, 2nd ed., ed. by R. E. Kendrick, G. H. M. Kronenberg, Kluwer Academic Publishers, Dordrecht, The Netherlands, 1994.
18. N. Frankenberg, K. Mukougawa, T. Kohchi, J. C. Lagarias, Plant Cell 2001, 13, 965.
19. T. Hübschmann, T. Börner, E. Hartmann, T. Lamparter, Eur. J. Biochem. 2001, 268, 2055.
20. S. H. Wu, M. T. McDowell, J. C. Lagarias, J. Biol. Chem. 1997, 272, 25700.
21. A.Blumenstein, K. Vienken, R. Tasler, J. Purschwitz, D. Veith, N. Frankenberg-Dinkel, R. Fischer, Curr. Biol. 2005, 15, 1833;
22. I. Oberpichler, I. Molina, O. Neubauer, T. Lamparter, FEBS Lett. 2006, 580, 437.
23. T. Lamparter, N. Michael, O. Caspani, T.Miyata, K. Shirai, K. Inomata, J. Biol. Chem. 2003, 278, 33786.
24. J. R. Wagner, J. S. Brunzelle, K. T. Forest, R. D. Vierstra, Nature 2005, 438, 325;
25. J. R. Wagner, J. Zhang, J. S. Brunzelle, R. D. Vierstra, K. T. Forest, J. Biol. Chem. 2007, 282, 12298;
26. X. Yang, E. A. Stojkovic, J. Kuk, K. Moffat, Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 12571;
27. X. Yang, J. Kuk, K. Moffat, Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 14715;
28. X. Yang, J. Kuk, K. Moffat, Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 15639.
29. W. Rüdiger, F. Thümmler, E. Cmiel, S. Schneider, Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 6244.
30. K. Inomata, Bull. Chem. Soc. Jpn. 2008, 81, 25, and references cited therein.
31. M. A. S. Hammam, H. Nakamura, Y. Hirata, H. Khawn, Y. Murata, H. Kinoshita, K. Inomata, Bull. Chem. Soc. Jpn. 2006, 79, 1561.
32. Preliminary communication of the synthesis of 15E-anti BV derivative: H. Kinoshita, M. A. S. Hammam, K. Inomata, Chem. Lett. 2005, 34, 800.
33. K. Inomata, M. A. S. Hammam, H. Kinoshita, Y. Murata, H. Khawn, S. Noack, N. Michael, T. Lamparter, J. Biol. Chem. 2005, 280, 24491;
34. K. Inomata, S. Noack, M. A. S. Hammam, H. Khawn, H. Kinoshita, Y. Murata, N. Michael, P. Scheerer, N. Krauss, T. Lamparter, J. Biol. Chem. 2006, 281, 28162.
35. H. Khawn, L.-Y. Chen, H. Kinoshita, K. Inomata, Chem. Lett. 2008, 37, 198.
36. K. Inomata, H. Khawn, L.-Y. Chen, H. Kinoshita, B. Zienicke, I. Molina, T. Lamparter, Biochemistry 2009, 48, 2817.
37. L.-Y. Chen, H. Kinoshita, K. Inomata, Chem. Lett. 2009, 38, 602.
38. P. Scheerer, N. Michael, J. H. Park, S. Nagano, H.-W. Choe, K. Inomata, B. Borucki, N. Krauß, T. Lamparter, ChemPhysChem 2010, 11, 1090.
39. A. T. Ulijasz, G. Cornilescu, C. C. Cornilescu, J. Zhang, M. Rivera, J. L. Markley, R. D. Vierstra, Nature 2010, 463, 250.
40. E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1965, 87, 1345.
41. In the B- and C-rings of the obtained PCB derivative, two tautomeric forms such as 12 and 12 are possible. In this manuscript, one of the tautomeric forms is shown in the schemes including the case of BV derivative.
42. D. H. R. Barton, J. Kervagoret, S. Z. Zard, Tetrahedron 1990, 46, 7587.
43. K. P. Jayasundera, H. Kinoshita, K. Inomata, Bull. Chem. Soc. Jpn. 2000, 73, 497.
44. N. Kornblum, J. Powers, J. Org. Chem. 1957, 22, 455.
45. R. M. Silverstein, E. E. Ryskiewicz, C. Willard, Org. Synth., Coll. Vol. 1963, IV, 831.
46. H. Kinoshita, H. Ngwe, K. Kobori, K. Inomata, Chem. Lett. 1993, 1441;
47. K. Kohori, M. Hashimoto, H. Kinoshita, K. Inomata, Bull. Chem. Soc. Jpn. 1994, 67, 3088.
48. K. P. Jayasundera, H. Kinoshita, K. Inomata, Chem. Lett. 1998, 1227.