Synthesis of fluorinated sphinganine and dihydroceramide analogues

European Journal of Organic Chemistry

Volumn , Issue 18, 2000, Pages 3177-3183

  De Jonghe, Steven ^a   Van Overmeire, Ilse ^a   Van Calenbergh, Serge ^a   Hendrix, Chris ^b   Busson, Roger ^b   De Keukeleire, Denis ^a   Herdewijn, Piet ^a,b  

^a GHENT UNIVERSITY   (Belgium)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Dihydroceramides; Enzyme inhibitors; Fluorination; Natural products; Sphinganines; Sphingolipids

Indexed keywords

3 FLUORODIHYDROCERAMIDE; 3 FLUOROSPHINGANINE; CERAMIDE DERIVATIVE; ENZYME INHIBITOR; FLUORIDE; FLUORINE; N[2 FLUORO 1(HYDROXYMETHYL)UNDECYL]ACETAMIDE; N[2 FLUORO 1(HYDROXYMETHYL)UNDECYL]HEXANAMIDE; OXAZOLIDINONE DERIVATIVE; SPHINGANINE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CYCLIZATION; FLUORINATION; LIPOGENESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS;

EID: 0033808604     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. C. S. Sweeley, Biochemistry of Lipids, Lipoproteins and Membranes (Eds.: D. E. Vance, J. Vance), Elsevier, Amsterdam, 1991, pp. 327-361.
2. K. Hirschberg, J. Rodger, A. H. Futerman, Biochem. J. 1993, 290, 751-757.
3. [3a] C. Michel, G. van Echten-Deckert, J. Rother, K. Sandhoff, E. Wang, A. H. Merrill, Jr., J. Biol. Chem. 1997, 272, 22432-22437.
4. [3b] C. Michel, G. van Echten-Deckert, FEBS Lett. 1997, 416, 153-155.
5. [3c] L. Geeraert, G. P. Mannaerts, P. P. Van Veldhoven, Biochem. J. 1997, 327, 125-132.
6. Y. A. Hannun, C. M. Linardic, Biochim. Biophys. Acta 1993, 1154, 223-236.
7. A. Bielawska, H. M. Crane, D. Liotta, L. M. Obeid, Y. A. Hannun, J. Biol. Chem. 1993, 268, 26226-26232.
8. [6a] W. D. Jarvis, R. N. Kolesnick, F. A. Fornari, R. S. Traylor, D. A. Gewirtz, S. Grant, Proc. Natl. Acad. Sci. USA 1994, 91, 73-77.
9. [6b] T. Wieder, C. C. Geilen, T. Kolter, F. Sadeghlar, K. Sandhoff, R. Brossmer, P. Ihrig, D. Perry, C. E. Organos, Y. A. Hannun, FEBS Lett. 1997, 411, 260-264.
10. G. van Echten, K. Sandhoff, J. Biol. Chem. 1993, 268, 5341-5344.
11. A. H. Futerman, B. Stieger, A. L. Hubbard, R. E Pagano, J. Biol. Chem. 1990, 265, 8650-8657.
12. I. Van Overmeire, S. A. Boldin, F. Dumont, S. Van Calenbergh, G. Slegers, D. De Keukeleire, A. H. Futerman, P. Herdewijn, J. Med. Chem. 1999, 42, 2697-2705.
13. J. T. Welch, Tetrahedron 1987, 43, 3123-3197.
14. P. Herold, Helv. Chim. Acta 1988, 77, 354-361.
15. J. Yoshida, M. Nakagawa, H. Seki, T. Hino, J. Chem. Soc., Perkin Trans. 1 1992, 343-350.
16. J. A. Wilkinson, Chem. Rev. 1992, 92, 505-519.
17. W. J. Middleton, J. Org. Chem. 1975, 40, 574-578
18. K. Bannai, T. Toru, T. Oba, T. Tanaka, N. Okamura, K. Watanabe, A. Hazato, K. Seki, Tetrahedron 1983, 39, 3807-3819.
19. P. J. Card, G. S. Reddy, J. Org. Chem. 1983, 48, 4734-4743.
20. P. Herdewijn, A. Van Aerschot, L. Kerremans, Nucleosides Nucleotides 1989, 8, 65-96.
21. S. Rozen, Y. Faust, H. Ben-Yakov, Tetrahedron Lett. 1979, 20, 1823-1826.
22. S. Futagawa, T. Inui, T. Shiba, Bull. Chem. Soc. Jpn. 1973, 46, 3308-3310.
23. C. Agami, F. Couty, L. Hamon, O. Venier, Tetrahedron Lett. 1993, 34, 4509-4512.
24. A. Tuch, M. Sanière, Y. Le Merrer, J. Depezay, Tetrahedron: Asymmetry 1996, 7, 897-906.
25. R. Wild, R. R. Schmidt, Tetrahedron: Asymmetry 1994, 5, 2195-2208.
26. L. Williams, Z. Zhang, F. Shao, P. J. Carroll, M. M. Joullié, Tetrahedron 1996, 52, 11673-11694.
27. B. Doboszewski, G. W. Hay, W. A. Szarek, Can. J. Chem. 1987, 65, 412-419.
28. [25a] P. Garner, J. M. Park, J. Org. Chem. 1987, 52, 2361-2364.
29. [25b] J. A. Marshall, S. Beaudoin, J. Org. Chem. 1996, 61, 581-586.
30. [26a] A. Kisie, M. Tsuda, R. J. Kulmacz, W. K. Wilson, G. J. Schroepfer, Jr., J. Lipid Res. 1995, 36, 787-803.
31. [26b] P. Tkaczuk, E. R. Thornton, J. Org. Chem. 1981, 46, 4393-4398.
32. C. Michel, G. van Echten-Deckert, J. Rother, K. Sandhoff, E. Wang, A. H. Merrill, Jr., J. Biol. Chem. 1997, 272, 22432-22437.
33. S. De Jonghe, I. Van Overmeire, J. Gunst, A. De Bruyn, C. Hendrix, S. Van Calenbergh, R. Busson, D. De Keukeleire, J. Philippé, P. Herdewijn, Bioorg. Med. Chem. Lett. 1999, 9, 3159-3164.