Synthesis of azide-fluoro-dehydrocoelenterazine analog as a photoaffinity-labeling probe and photolysis of azide-fluoro-coelenterazine

Tetrahedron

Volumn 61, Issue 24, 2005, Pages 5754-5762

  Kuse, Masaki ^a   Doi, Issei ^a   Kondo, Nobuhiro ^a   Kageyama, Yukari ^a   Isobe, Minoru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Azide fluoro phenyl; Coelenterazine; Deuteriation MS; Exchangeable protons; Photoaffinity probe

Indexed keywords

4 FLUOROPHENYLACETIC ACID; ACETIC ACID DERIVATIVE; AZIDE; AZIDE FLUOROCOELENTERAZINE; AZIDE FLUORODEHYDROCOELENTERAZINE; DEUTERIUM; LECTIN; PHOTOPROTEIN; PROTON; SYMPLECTIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHROMATOPHORE; MASS SPECTROMETRY; MEASUREMENT; NONHUMAN; OXIDATION; PHOTOAFFINITY LABELING; PHOTOLYSIS; PHOTOREACTIVITY; PRIORITY JOURNAL; SYNTHESIS;

EID: 19744370633     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.04.025     Document Type: Article

References (27)

1. F.I. Tsuji, and G. Leisman Proc. Natl. Acad. Sci. U.S.A. 78 1981 6719 6723
2. H. Takahashi, and M. Isobe Bioorg. Med. Chem. Lett. 3 1993 2647 2652
3. H. Takahashi, and M. Isobe Chem. Lett. 1994 843 846
4. M. Isobe, M. Kuse, Y. Yasuda, and H. Takahashi Bioorg. Med. Chem. Lett. 8 1998 2919 2924
5. M. Kuse, and M. Isobe Tetrahedron 56 2000 2629 2639
6. T. Fujii, J.Y. Ahn, M. Kuse, H. Mori, T. Matsuda, and M. Isobe Biochem. Biophys. Res. Commun. 293 2002 874 879
7. M.L. Souto, J. Um, B. Borhan, and K. Nakanishi Helv. Chim. Acta 83 2000 2617 2628
8. G. Dorman, and G.D. Prestwich Trends Biotechnol. 18 2000 64 77
9. M. Kurono, A. Shimomura, and M. Isobe Tetrahedron 60 2004 1773 1780
10. J.L. Zheng, F.Q. Chen, T. Hirano, Y. Ohmiya, S. Maki, H. Niwa, and M. Ohashi Bull. Chem. Soc. Jpn. 73 2000 465 469
11. R. Poe, K. Scnapp, M.J.T. Young, J. Grayzar, and M.S. Platz J. Am. Chem. Soc. 114 1992 5054 5067
12. M.S. Platz R.A. Moss M.S. Platz M. Jones Jr. Reactive intermediate chemistry 2004 Wiley New Jersey 501 559
13. M. Isobe, T. Fujii, M. Kuse, K. Miyamoto, and K. Koga Tetrahedron 58 2002 2117 2126
14. Y. Kita, H. Tohma, M. Inagaki, K. Hatanaka, and T. Yakura Tetrahedron 32 1991 4321 4324
15. Y. Kishi, H. Tanino, and T. Goto Tetrahedron Lett. 13 1972 2747 2748
16. H. Kakoi Chem. Pharm. Bull. 50 2002 301 302
17. S. Inoue, S. Sugiura, H. Kakoi, K. Hashizume, T. Goto, and H. Iio Chem. Lett. 1975 141 144
18. Recently, we reported the alternative synthetic route for various 6-substituted coelenteramine analogs: M. Kuse, N. Kondo, Y. Ohyabu, and M. Isobe Tetrahedron 60 2004 835 840
19. K.G. Pinney, and J.A. Katzenellenbogen J. Org. Chem. 56 1991 3125 3133
20. J. Head, S. Inoue, K. Teranishi, and O. Shimomura Nature 405 2000 372 376
21. K. Usami, and M. Isobe Tetrahedron Lett. 36 1995 8613 8616
22. K. Usami, and M. Isobe Tetrahedron 52 1996 12061 12090
23. T. Kurahashi, A. Miyazaki, S. Suwan, and M. Isobe J. Am. Chem. Soc. 123 2001 9268 9278
24. 26 This may be responsible for the fluorine atom, which prevents carbon migration to the nitrene due to its electronegativity. (Chemical Equation Presented).
25. M. Kuse, A. Kanakubo, S. Suwan, K. Koga, M. Isobe, and O. Shimomura Bioorg. Med. Chem. Lett. 11 2001 1037 1040
26. A. Kanakubo, and M. Isobe J. Mass Spectrom. 39 2004 1260 1267
27. We considered the possibility for the ring expansion of the nitrene intermediate. If ring expansion happened, the resultant azepine derivative (22) also has four exchangeable protons. However, the initial fragmentation product observed at m/z 439 should have three exchangeable protons. If this is the case, m/z 442 should be observed in deuterium solvent. Thus, the peak at m/z 443 in Figure 4I was critical to exclude the possibility of ring expansion product (22). (Chemical Equation Presented).