Structural elucidation of ciguatoxin congeners by fast-atom bombardment tandem mass spectroscopy [5]

Journal of the American Chemical Society

Volumn 122, Issue 20, 2000, Pages 4988-4989

  Yasumoto, Takeshi ^a   Igarashi, Tomoji ^a   Legrand, Anne Marie ^b   Cruchet, Philippe ^b   Chinain, Mireille ^b   Fujita, Tsuyoshi ^c   Naoki, Hideo ^c  

^a JAPAN FOOD RESEARCH LABORATORIES   (Japan)

^b Inst Terr Rech Medicales Louis M   (French Polynesia)

^c SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CIGUATOXIN;

DRUG STRUCTURE; LETTER; LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; TANDEM MASS SPECTROMETRY;

EID: 0034709383     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9944204     Document Type: Letter

References (18)

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2. Satake, M.; Ishihashi, Y.; Legrand, A-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1997, 60, 2103-2105.
3. Murata, M.; Legrand, A-M.; Ishibashi, Y.; Yasumoto, T. J. Am. Chem. Soc. 1989, 111, 8929-8931.
4. Satake, M.; Murata, M.; Yasumoto, T. Tetrahedron Lett. 1993, 34, 1975-1978.
5. Satake, M.; Morohashi, A.; Oguri, H.; Oishi, T.; Hirama, M.; Harada, N.; Yasumoto, T. J. Am. Chem. Soc. 1997, 119, 11325-11326.
6. 3 and silicic acid were not used.
7. Adams, J. Mass Spectrom. Rev. 1990, 9, 141-186.
8. (a) Naoki, H.; Murata, M.; Yasumoto, T. Rapid Comm. Mass Spectrom. 1993, 7, 179-182.
9. (b) Murata, M.; Naoki, H.; Iwashita, T.; Matsunaga, S.; Sasaki, M.; Yokoyama, A.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 2060-2062.
10. (c) Murata, K.; Satake, M.; Naoki, H.; Kaspar, H. F.; Yasumoto, T. Tetrahedron 1998, 54, 735-742.
11. (d) Morohashi, A.; Satake, M.; Murata, K.; Naoki, H.; Kaspar, H. F.; Yasumoto, T. Tetrahedron Lett. 1995, 36, 8995-8998.
12. (e) Morohashi, A.; Satake, M.; Naoki, H.; Kaspar, H. F.; Oshima, Y.; Yasumoto, T. Natural Toxins 1999, 7, 45-48.
13. (f) Satake, M.; Ofuji, K.; Naoki, H.; James, K. J.; Furey, A.; MacMahon, T.; Silke, J.; Yasumoto, T. J. Am. Chem. Soc. 1988, 120, 9967-9968.
14. 2O (8:1:1) were used for LC/MS.
15. 3.
16. 2 stream and the residue was dissolved in the HPLC mobile phase. MM2 calculations on spiro rings IVM indicate that 52R/54SOH configuration in 1 is more stable (minimum energy 336.59 kJ/mol) than 525/54SOH configuration in 9 (minimum energy 351.88 kJ/mol). The same is true with rings L/M in 2 (49R, 306.14 kJ/mol) and 3 (49S, 321.85 kJ/mol).
17. Lewis, R. J.; Norton, R. S.; Brereton, I. M.; Eccles, C. D. Toxicon 1993, 31, 637-643. The same toxin prepared and confirmed in Yasuomoto's laboratory was used.
18. Satake, M.; Fukui, M.; Legrand, A-M.; Cruchet, P.; Yasumoto, T. Tetrahedron Lett. 1998, 39, 197-1198.