A general and stereoselective route to α- or β- galactosphingolipids via a common four-carbon building block

Journal of Organic Chemistry

Volumn 72, Issue 20, 2007, Pages 7757-7760

  Matto, Pamela ^a   Modica, Emilia ^a   Franchini, Laura ^a   Facciotti, Federica ^b   Mori, Lucia ^b   De Libero, Gennaro ^b   Lombardi, Grazia ^c   Fallarini, Silvia ^c   Panza, Luigi ^c   Compostella, Federica ^a   Ronchetti, Fiamma ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY HOSPITAL BASEL   (Switzerland)

^c UNIVERSITY OF EASTERN PIEDMONT   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYLATION; CARBON BUILDING BLOCKS; GALACTOSPHINGOLIPIDS; STEREOCENTERS;

AMIDES; CARBON; CHEMICAL BONDS; MOLECULAR STRUCTURE; REACTION KINETICS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

LIPIDS;

3 AZIDO 2 O BENZYL 1 O (4 METHOXYBENZYL)BUTANE 1,2,4 TRIOL; ALPHA GALACTOSPHINGOLIPID DERIVATIVE; AZIDE; BENZYL DERIVATIVE; BETA GALACTOSPHINGOLIPID DERIVATIVE; BUTANOL; CARBON; GALACTOSYLCERAMIDE; GLYCOLIPID; LIPID; PHYTOSPHINGOSINE; SPHINGOLIPID; SPHINGOSINE; UNCLASSIFIED DRUG;

ALKYNYLATION; ANIMAL CELL; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; HORNER REACTION; LIGHT CHAIN; NONHUMAN; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; T LYMPHOCYTE;

ADJUVANTS, IMMUNOLOGIC; ANIMALS; GALACTOSE; GALACTOSYLCERAMIDES; LYMPHOCYTE ACTIVATION; MICE; STEREOISOMERISM; T-LYMPHOCYTES;

EID: 34848902594     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070849z     Document Type: Article

References (36)

1. (a) De Libero, G.; Mori, L. Nature Rev. Immunol. 2005, 5, 485-496.
2. (b) Moody, D. B.; Zajonc, D. M.; Wilson, I. A. Nature Rev. Immunol. 2005, 5, 387-399.
3. (c) Lawton, A. P.; Kronenberg, M. Immunol. Cell Biol. 2004, 82, 295-306.
4. (d) De Libero, G.; Mori, L. Trends Immunol. 2006, 27, 485-492.
5. (a) Morita, 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. (b) Kawano, T.; Cui, J. Q.; Koezuka, Y.; Toura, I.; Kaneko, Y.; Motoki, K.; Ueno, H.; Nakagawa, R.; Sato, H.; Kondo, E.; Koseki, H.; Taniguchi, M. Science 1997, 278, 1626-1629.
7. (a) Savage, P. B.; Teyton, L.; Bendelac, A. Chem. Soc. Rev. 2006, 35, 771-779.
8. (b) Brutkiewicz, R. R. J. Immunol. 2006, 177, 769-775.
9. (a) Van Kaer, L. Nature Rev. Immunol. 2005, 5, 31-42.
10. (b) Bendelac, A.; Savage, P. B.; Teyton, L. Annu. Rev. Immunol. 2007, 25, 297-336.
11. (a) Porcelli, S. A. Ceramide derivatives as modulators of immunity and autoimmunity. U.S. Patent 2006/0052316, Mar 9, 2006.
12. (b) Goff, R. D.; Gao, Y.; Mattner, J.; Zhou, D.; Yin, N.; Cantu, C.; Teyton, L.; Bendelac, A.; Savage, P. B. J. Am. Chem. Soc. 2004, 126, 13602-13603.
13. (c) Schmieg, J.; Yang, G.; Franck, R. W.; Tsuji, M. J. Exp. Med. 2003, 198, 1631-1641.
14. (d) Yang, G.; Schmeig, J.; Tsuji, M.; Franck, R. W. Angew. Chem., Int. Ed. 2004, 43, 3818-3822.
15. (a) Shamshiev, A.; Donda, A.; Carena, L.; Mori, L.; Kappos, L.; De Libero, G. Eur. J. Immunol. 1999, 29, 1667-1675.
16. (b) Shamshiev, A.; Gober, H. J.; Donda, A.; Mazorra, Z.; Mori, L.; De Libero, G. J. Exp. Med. 2002, 195, 1013-1021.
17. (a) Compostella, F.; Franchini, L.; De Libero, G.; Palmisano, G.; Ronchetti, F.; Panza, L. Tetrahedron 2002, 58, 8703-8708.
18. (b) Compostella, F.; Ronchi, S.; Panza, L.; Mariotti, S.; Mori, L.; De Libero, G.; Ronchetti, F. Chem. - Eur. J. 2006, 12, 5587-5595.
19. (c) Modica, E.; Compostella, F.; Colombo, D.; Franchini, L.; Cavallari, M.; Mori, L.; De Libero, G.; Panza, L.; Ronchetti, F. Org. Lett. 2006, 8, 3255-3258.
20. For related flexible strategies, see, for example: (a) Rai, A. N.; Basu, A. J. Org. Chem. 2005, 70, 8228-8230.
21. (b) Barrett, A. G. M.; Beall, J. C.; Braddock, D. C.; Flack, K.; Gibson, V. C.; Salter, M. M. J. Org. Chem. 2000, 65, 6508-6514.
22. (c) Reference 5a.
23. (d) Howell, A. R.; So, R. C.; Richardson, S. K. Tetrahedron 2004, 60, 11327-11347.
24. (d) Bundle, D. R.; Ling, C. C.; Zhang, P. Synthetic methods for the large scale production from glucose of analogs of sphingosine, azidosphingosine, ceramides, lactosyl ceramides, and glycosyl phytosphingosine. WO 03/101937 A1, Dec 11, 2003.
25. (e) Du, W.; Kulkarni, S. S.; Gervay-Hague, J. Chem. Commun. 2007, 2336-2338.
26. Franchini, L.; Compostella, F.; Donda, A.; Mori, L.; Colombo, D.; De Libero, G.; Matto, P.; Ronchetti, F.; Panza, L. Eur. J. Org. Chem. 2004 4755-4761.
27. (a) Shingu, Y.; Nishida, Y.; Dohi, H.; Kobayashi, K. Org. Biomol. Chem. 2003, 1, 2518-2521.
28. (b) Nishida, Y.; Shingu, Y.; Dohi, H.; Kobayashi, K. Org. Lett. 2003, 5, 2377-2380.
29. Frantz, D. E.; Fässler, R.; Tomooka, C. S.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373-381.
30. For our synthetic purposes we only isolated the major product, having the proper R-configuration. Therefore, the diasteroselectivity of the reaction was not investigated.
31. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
32. (b) Devijver, C.; Salmoun, M.; Daloze, D.; Braekman, J. C.; De Weerdt, W. H.; De Kluijver M. J.; Gomez, R. J. Nat. Prod. 2000, 63, 978-980.
33. (c) Chun, J.; Byun, H.-S.; Arthur, G.; Bittman, R. J. Org. Chem. 2003, 68, 355-39.
34. Zimmermann, P.; Bommer, R.; Bär, T.; Schmidt, R. R. J. Carbohydr. Chem. 1988, 7, 435-452.
35. Schümann, J.; Facciotti, F.; Panza, L.; Michieletti, M.; Compostella, F.; Collmann, A.; Mori, L.; De Libero, G. Eur. J. Immunol. 2007, 37, 1431-1441.
36. McCarthy, C.; Shepherd, D.; Fleire, S.; Strenge, V. S.; Koch, M.; Illarionov, P. A.; Bossi, G.; Salio, M.; Denkberg, G.; Reddington, F.; Tarlton, A.; Reddy, B. G.; Schmidt, R. R.; Reiter, Y.; Griffiths, G. M.; van der Merwe, P. A.; Besra, G. S.; Jones, E. Y.; Batista, F. D.; Cerundolo, V. J. Exp. Med. 2007, 204, 1131-1144.