Synthesis of cyclic sphingosine 1,3-phosphate (cSPP) through a photolytic reaction

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 8959-8962

  Qiao, Lixin ^a   Kozikowski, Alan P ^a  

^a GEORGETOWN UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SPHINGOSINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; PHOSPHOLIPID SYNTHESIS; PHOSPHORYLATION;

EID: 0032480932     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02071-1     Document Type: Article

References (24)

1. 1 For reviews, see: (a) Hannun, Y. A. Science 1996, 274, 1855.
2. (b) Spiegel, S.; Merrill, A. H. Jr. FASEB J. 1996, 10, 1388.
3. (c) Igarashi, Y. J. Biochem. (Japan) 1997, 122, 1080.
4. 2 Cuvillier, O.; Pirianov, G.; Kleuser, B.; Vanek, P. G.; Coso, O. A.; Gutkind, S.; Spiegel, S. Nature 1996, 381, 800.
5. 3 Mattie, M.; Brooker, G.; Spiegel, S. J. Biol. Chem. 1994, 269, 3181
6. 4 Goodenite, K. A.; Mattie, M. E.; Berger, A.; Spiegel, S. J. Biol. Chem. 1995, 270, 10272.
7. 5 Conway, A. M.; Pyne, N. J.; Pyne, S. Biochem. Soc. Trans. (England) 1997, 25, S585.
8. 6 Lee, M.; Brooklyn, J. R. V.; Thangada, S.; Liu, C. H.; Hand, A. R.; Menzeleev, R.; Spiegel, S.; Hla, T. Science 1998, 279, 1552.
9. 7 Ruan, F.; Sadahira, Y.; Hakomori, S.; Ifarashi, Y. Bioorg. Med. Chem. Lett. 1992, 2, 973.
10. 8 Kratzer, B.; Schmidt, R. R. Tetrahedron Lett. 1993, 34, 1761.
11. 9 Boumendjel, A.; Miller, S. P. F. J. Lipid Res. 1994, 35, 2305.
12. 10 (a) For a review, see: Byun, H.; Bittman, R. In Phospholipids Handbook; Cevc, G., Ed.; Marcel Dekker: New York, 1993; 97-140.
13. For recent activities, see: (b) Nugent, T. C.; Hundlicky, T. J. Org. Chem. 1998, 63, 510.
14. (c) Byun, H.; Sadlofsky, J. A.; Bittman, R. J. Org. Chem. 1998, 63, 2560, and references cited therein.
15. 11 Qiao, L.; Kozikowski, A. P.; Olivera, A.; Spiegel, S. Bioorg. Med. Chem. Lett. 1998, 8, 711.
16. 12 Boudker, O.; Futerman, A. H. J. Biol. Chem. 1993, 268, 22150.
17. 13 Pillai, V. N. R. Synthesis 1980, 1.
18. 14 Walker, J. W.; Gilbert, S. H.; Drummond, R. M.; Yamada, M.; Sreekumar, R.; Carraway, R. E.; Ikebe, M.; Fay, F. S. Proc. Natl. Acad. Sci. USA 1998, 95, 1568.
19. 15 Rossi, F. M.; Margulis, M.; Tang, C. M.; Kao, J. P. J. Biol. Chem. 1997, 272, 32933.
20. 16 Zehavi, U. Chem. Phys. Lipids 1997, 90, 55.
21. 17 Broustovetsky, N.; Bamberg, E.; Gropp, T.; Klingenberg, M. Biochemistry 1997, 36, 13865.
22. 2. The resulting mixture was stirred at 0 °C for another hour before filtration through Celite. The filtrate was concentrated in a well-ventilated hood affording desired chloroformate 2, which was used directly in the next step without further purification.
23. +, 362.2460; found, 362.2446.
24. 3OD 1/1 (v/v), TMS) δ 2.87 correlates with δ 4.39, δ 4.15, and δ 3.98; δ 4.39 correlates with δ 5.30 and δ 2.87 only; δ 4.15 and δ 3.98 correlate with each other, and with δ 2.87.