Synthesis of 13C-dehydrocoelenterazine and model studies on Symplectoteuthis squid bioluminescence

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 20, 1998, Pages 2919-2924

  Isobe, Minoru ^a   Kuse, Masaki ^a   Yasuda, Yoshio ^a   Takahashi, Hiroyuki ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DEHYDROCOELENTERAZINE; PHOTOPROTEIN; UNCLASSIFIED DRUG; CARBON; IMIDAZOLE DERIVATIVE; PYRAZINE DERIVATIVE;

ARTICLE; BIOLUMINESCENCE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; NONHUMAN; REACTION ANALYSIS; SQUID; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; ANIMAL; CEPHALOPOD; CHEMISTRY; LUMINESCENCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ULTRAVIOLET SPECTROPHOTOMETRY;

ANIMALS; CARBON ISOTOPES; DECAPODIFORMES; IMIDAZOLES; LUMINESCENCE; LUMINESCENT PROTEINS; MAGNETIC RESONANCE SPECTROSCOPY; PYRAZINES; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0032552728     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00525-3     Document Type: Article

References (17)

1. 1 Isobe, M.; Takahashi, H.; Usami, K.; Hattori, M.; Nishigohri, Y. Pure Appl. Chem. 1994, 66, 765-772.
2. 2 Tsuji, F. I.; Leisman, G. Proc. Natl. Acad. Sci. U. S. A. 1981, 78, 6719-6723.
3. 3 Takahashi, H.; Isobe, M. Biomed. Chem. Lett. 1993, 3, 2647-2652.
4. 4 Takahashi, H.; Isobe, M. Chem. Lett. 1994, 843-846.
5. 5 a) Usami, K.; Isobe, M. Tetrahedron Lett. 1995, 36, 8613-8616.
6. b) Usami, K.; Isobe, M. Tetrahedron 1996, 52, 12061-12090.
7. 6 a) Goto, T.; Iio, H.; Inoue, S.; Kakoi, H. Tetrahedron Lett. 1974, 2321-2324,
8. b) Inoue, S.; Taniguchi, H.; Murata, M.; Kakoi, H.; Goto, T. Chem. Lett. 1977, 259-262.
9. 13C-enriched coelenterazines we need; a) Hirano, T.; Negishi, R.; Yamaguchi, M.; Chen, F. Q.; Ohmiya, Y.; Tsuji, F. I.; Ohashi, M. Tetrahedron 1997, 53, 12903-12916.
10. b) Keenan, M.; Jones, K.; Hibbert, F. Chem. Comm. 1997, 323-324.
11. c) Nakamura, H.; Takeuchi, D.; Murai, A. Synlett 1995, 1227-1228.
12. 8 Kishi, Y.; Tanino, H.; Goto, T. Tetrahedron Lett. 1972, 2747-2750.
13. 9 Gassman, P. G.; Talley, J. J. Tetrahedron Lett. 1978, 3773-3776. Trimethylsilyl cyanide was prepared according to the method described in ref. # 5a.
14. 10 Bromohydrin (16) rearranged and then converted into various products at higher temperatures.
15. 11 a) Isobe, M.; Iio, H.; Kawai, T.; Goto, T. Tetrahedron Lett. 1977, 703-706.
16. b) Iio, H.; Isobe, M.; Kawai, T.; Goto, T. Tetrahedron 1979, 35, 941-948.
17. +).