Lipase-catalyzed enantiomeric resolution of ceramides 1

Journal of Organic Chemistry

Volumn 63, Issue 20, 1998, Pages 6929-6938

  Bakke, Mikio ^a   Takizawa, Masahiro ^a   Sugai, Takeshi ^a   Ohta, Hiromichi ^a   Herold, P ^b  

^a KEIO UNIVERSITY   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000287958     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980727u     Document Type: Article

References (26)

1. Reviews: bhapiro, D. In Chemistry of Sphingolipids; Herman-Verlag: Paris, 1969. Stoffel, W. Chem. Phys. Lipids 1973, 11, 318-334.
2. Ha'komori, S.; Zhang, Y. Chem. Biol. 1997,4, 97-104.
3. Kolter, T.; Sandhoff, K. Chem. Soc. Rev. 1996, 25, 371-381. Kolter, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1955-1959.
4. Hannun, Y. A.; Bell, R. M. Science 1989,243, 500-507.
5. Monta, M.; Motoki, K.; Akimoto, K; Natori, T.; Sakai, T.; Sawa, E.; Yamaji, K.; Koezuka, Y.; Kobayashi, E.; Fukushima, H. J. Med. Chem. 1995, 38,2176-2187.
6. Ikeda, K; Asahara, T.; Achiwa, K; Hoshino, H. Chem. Pharm. Bull. 1997, 45, 402-405.
7. Kawano, T.; Gui, J.; Koezuka, Y.; Toura, L; Kaneko, Y.; Motoki, K.; Ueno, H.; Nakagawa, R.; Sato, H.; Kondo, E.; Koseki, H.; Taniguchi, M. Science 1997, 278, 1626-1629.
8. Syntheses of racemic forms via nitroaldol reactions: (a) Grob, C. A.; Gadient, F. Helv. Chim. Acta 1957, 40, 1145-1157.
9. (b) Mori, K; Funaki, Y. Tetrahedron 1985, 41, 2369-2377.
10. Hino, T.; Nakayama, K; Taniguchi, M.; Nakagawa, M. J. Chem. Soc., Perkin Trans. 11986,1687-1690.
11. Umemura, T.; Mori, K.Agric. Biol. Chem. 1987, 51, 217-224.
12. (e) Kodato, S.; Nakagawa, M.; Nakayama, K.; Hino, T. Tetrahedron 1989,45, 7247-7262.
13. (f) Kolter, T.; van Echten-Deckert, G.; Sandhoff, K. Tetrahedron 1994, 50, 13425-13432.
14. Syntheses of racemic forms starting from glycine: (a) Schmidt, R. R.; Kläger, R. Angew. Chem., Int. Ed. Engl. 1982,21, 210-211.
15. (b) Schmidt, R. R.; Kläger, R. Angew. Chem. Suppl. 1982, 393-397.
16. Schmidt, R. R.; Kläger, R. Angew. Chem., Int. Ed. Engl. 1985,24, 65-66.
17. Other Syntheses of racemic forms: (a) Jenny, E. F.; Grob, C. A. Helv. Chim. Acta 1953,36, 1936-1944.
18. (b) Shapiro, D.; Sheradsky, T. J. Org. Chem. 1963, 28, 2157.
19. Sisido, K.; Hirowatari, N.; Isida, T. J. Org. Chem. 1964,29, 2783-2784.
20. Garigipati, R. S.; Weinreb, S. M. J. Am. Chem. Soc. 1983, 705, 4499-4501.
21. (e) Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1986, 42, 917-922.
22. Syntheses of optically active forms starting from amino acids: (a) New-man, H. J. Org. Chem. 1974, 39, 100-103.
23. (b) Tkaczuk, P.; Thomton, E. R. J. Org. Chem. 1981, 46, 4393-4398.
24. Mon, K.; Funaki, Y. Tetrahedron 1985, 41, 2379-2386.
25. Boutin, R. H.; Rapoport, H. J. Org. Chem. 1986,51,5320-5327.
26. (e) Garner, P.; Park, J. M.; Malecki, E. J. Org. Chem. 1988, 53, 4395-4398.