Practical synthesis of N-palmitoylsphingomyelin and N- palmitoyldihydrosphingomyelin

Methods in Enzymology

Volumn 311, Issue , 2000, Pages 535-547

  Bushnev, Anatoliy S ^a   Liotta, Dennis C ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

CERAMIDE; SPHINGOLIPID; SPHINGOMYELIN; SPHINGOSINE DERIVATIVE;

CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REVIEW; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032742651     PISSN: 00766879     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0076-6879(00)11104-8     Document Type: Article

References (46)

1. Y. A. Hannun and L. M. Obeid, Biochem. Soc. Trans. 25, 1171 (1997).
2. A. H. Merrill, Jr., E.-M. Schmelz, D. L. Dillehay, S. Spiegel, J. A. Shayman, J. J. Schroeder, R. T. Riley, K. A. Voss, and E. Wang, Toxicol Appl. Pharmacol. 142, 208 (1997).
3. P. K. Sripada, P. R. Maulik, J. A. Hamilton, and G. G. Shipley, J. Lipid Res. 28, 710 (1987).
4. K. Liliom, D. J. Fischer, T. Virág, G. Sun, D. D. Miller, J.-L. Tseng, D. M. Desiderio, M. C. Seidel, J. R. Erickson, and G. Tigyi, J. Blol. Chem. 273, 13461 (1998).
5. H. S. Byun, R. K. Erukulla, and R. Bittman, J Org. Chem. 59, 6495 (1994).
6. K. S. Bruzik, J. Chem. Soc. Chem. Commun. 329 (1986).
7. K. S. Bruzik, J. Chem. Soc. Perkin Trans. 1 423 (1988).
8. Z. Dong and J. A. Butcher, Jr., Chem. Phys. Lipids 66, 41 (1993).
9. B. Kratzer. T. G. Mayer, and R. R. Schmidt, Tetrahedron Lett. 34, 6881 (1993).
10. B. Kratzer and R. R. Schmidt, Liebigs Ann. 957 (1995
11. J. J. Gaudino, K. Bjergarde, P.-Y. Chan-Hui. C. D. Wright, and D. S. Thomson. Bioorg. Med. Chem. Lett. 7, 1127 (1997).
12. A. Yu. Frantova, A. S. Bushnev, E. N. Zvonkova, and V. I. Shvets, Bioorg. Khim. (Russian) 17, 1562 (1991).
13. P. Herold, Helv. Chim. Acta 71, 354 (1988).
14. P. Garner, J. Park, and E. Malecki, J. Org. Chem. 53, 4395 (1988).
15. H.-E. Radunz, R. Devant, and V. Eiermann, Liebigs Ann. Chem. 1103 (1988).
16. S. Nimkar, D. Menaldino, A. Merrill, and D. Liotta, Tetrahedron Lett. 29, 3037 (1988).
17. K. Mori and H. Matsuda, Liebigs Ann. Chem. 529 (1991).
18. T. Abe and K. Mori, Biosci. Biotechnol. Biochem. 58, 1671 (1994).
19. P. Garner and J. M. Park, J. Org. Chem. 52, 2361 (1987).
20. P. Garner and J. M. Park, Org. Synth. 70, 18 (1991).
21. A. Dondoni and D. Perrone, Synthesis 527 (1997).
22. J. S. R. Kumar and A. Datta, Tetrahedron Lett. 38, 6779 (1997).
23. A. Avenoza, C. Cativiela, F. Corzana, J. M. Peregrina, and M. M. Zurbano, Synthesis 1146 (1997).
24. M. Nakagawa, J. Yoshida, and T. Hino, Chem. Lett. 1407 (1990).
25. J. Yoshida, M. Nakagawa, H. Seki, and T. Hino, J. Chem. Soc. Perkin Trans, 1 343 (1992).
26. K. Mori and K. Uenishi, Liebigs Ann. Chem. 41 (1994).
27. O. V. Oskolkova, A. Y. Zamyatina, V. I. Shvets, D. S. Esipov, and V. G. Korobko, Bioorg. Khim. (Russian) 22, 307 (1996).
28. O. V. Oskolkova. A. V. Perepelov, D. S. Esipov, A. Y. Zamyatina, S. G. Alekseeva, and V. I. Shvets, Bioorg. Khim. (Russian) 23, 591 (1997).
29. A. Yu. Frantova, A. E. Stepanov, A. S. Bushnev, E. N. Zvonkova, and V. I. Shvets, Tetrahedron Lett. 33, 3539 (1992).
30. A. Y. Zamyatina, A. E. Stepanov, A. S. Bushnev, E. N. Zvonkova, and V. I. Shvets, Bioorg. Khim. (Russian) 19, 347 (1993).
31. A. Y. Zamyatina and V. I. Shvets, Chem. Phys. Liplds 76, 225 (1995).
32. B. Kratzer, T. G. Mayer, and R. R. Schmidt, Eur. J. Org. Chem. 291 (1998).
33. A. Boumendjel and S. P. F. Miller, J. Labeled Comp. Radiopharm. 36, 243 (1994).
34. B. Kratzer and R. R. Schmidt, Tetrahedron Lett. 34, 1761 (1993).
35. A. Boumendjel and S. P. F. Miller, J. Lipid Res. 35, 2305 (1994).
36. A. Yu. Zamyatina, A. S. Bushnev and V. I. Shvets, Bioorg. Khim. (Russian) 20, 1253 (1994).
37. S. L. Beaucage and R. P. Iyer, Tetrahedron 49, 10441 (1993).
38. E. E. Nifant'ev and D. A. Predvoditelev, Russian Chem. Rev. 63, 71 (1994).
39. E. E. Nifant'ev and M. K. Grachev, Russian Chem. Rev. 63, 575 (1994).
40. F. Paltauf and A. Hermetter, Prog. Lipid Res. 33, 239 (1994).
41. D. Shapiro, "Chemistry of Sphingolipids." Herman, Paris 1969.
42. D. Shapiro and H. M. Flowers, J. Am. Chem. Soc. 84, 1047 (1962).
43. In: T. W. Greene and P. G. M. Wuts, "Protective Groups in Organic Synthesis," 2nd ed., p. 309. Wiley, New York, 1984.
44. R. Villard, F. Fotiadu, and G. Buono, Tetrahedron: Asymmetry 9, 607 (1998).
45. L. Clary, C. Santaella, and P. Vierling, Tetrahedron 51, 13073 (1995).
46. T. Murakami, H. Minamikawa, and M. Hato, J. Chem. Soc. Perkin Trans. 1 1875 (1992).