Download PDF
Synthesis 2010(19): 3309-3314  
DOI: 10.1055/s-0030-1257944
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Enantiopure Fluorinated Ceramides; Analogues of Natural Sphingolipids

Katarzyna Koroniak, Günter Haufe*
Organisch-Chemisches Institut and NRW International Graduate School of Chemistry, Correnstraße 40, 48149 Münster, Germany
Fax: +49(251)8339772; e-Mail: haufe@uni-muenster.de;
Further Information

Publication History

Received 26 March 2010
Publication Date:
30 July 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

The synthesis of a series of different fluorinated analogues of sphinganine and dihydroceramide using Staudinger ligation of diastereomeric 2-azido-4-fluoro-3-hydroxyoctadecanoates and subsequent selective ester reduction as key steps is presented. The formed sphingolipid analogues are interesting for medicinal studies as well as for the investigation of their phase behavior at interfaces.

Key words

sphingolipids - asymmetric synthesis - acylation - fluorination - amides

    References

  • 1 Carter HE. Glick FJ. Norris WP. Phillips GE. J. Biol. Chem.  1947,  170:  285 
    Google Scholar
  • 2 Multiauthor series of minireviews on Sphingolipid Metabolism and Signaling: J. Biol. Chem.  2002,  277:  25841-25861  
    CrossrefGoogle Scholar
  • 3a Chalfant CE. Spiegel S. J. Cell Sci.  2005,  118:  4605 
    Google Scholar
  • 3b Woodcock J. IUBMB Life  2006,  58:  462 
    Google Scholar
  • 3c Kitatani K. Idkowiak-Baldys J. Hannun YA. Cell Signalling  2008,  20:  1010 
    Google Scholar
  • 4a Mao C. Obeid LM. Biochim. Biophys. Acta  2008,  1781:  424 
    Google Scholar
  • 4b Gangoiti P. Granado MH. Alonso A. Goñi FM. Gómez-Muñoz A. Translational Oncogenomics  2008,  3:  81 ; http://www.la-press.com/translational-oncogenomics-journal-j19
    Google Scholar
  • 4c Jana A. Hogan EL. Pahan K. J. Neurol. Sci.  2009,  278:  5 
    Google Scholar
  • 5a Koskinen PM. Koskinen AMP. Synthesis  1998,  1075 
    Google Scholar
  • 5b Curfman C. Liotta D. Methods Enzymol.  1999,  311:  391 
    Google Scholar
  • 5c Kolter T. Sandhoff K. Angew. Chem. Int. Ed.  1999,  38:  1532 ; Angew. Chem. 1999, 111, 1632
    Google Scholar
  • 5d Brodesser S. Sawatzki P. Kolter T. Eur. J. Org. Chem.  2003,  2021 
    Google Scholar
  • 5e Liao J. Tao J. Lin G. Liu D. Tetrahedron  2005,  61:  4715 
    Google Scholar
  • 6a Sawai H. Domae N. Okazaki T. Curr. Pharm. Des.  2005,  11:  2479 
    Google Scholar
  • 6b Huwiler A. Zangemeister-Wittke U. Crit. Rev. Oncol. Hematol.  2007,  63:  150 
    Google Scholar
  • 6c Nussbaumer P. ChemMedChem  2008,  3:  543 
    Google Scholar
  • 6d Hannun YA. Obeid LM. Nat. Rev. Mol. Cell Biol.  2008,  9:  139 
    Google Scholar
  • 7 Smart BE. J. Fluorine Chem.  2001,  109:  3 
    CrossrefGoogle Scholar
  • 8 O’Hagan D. Rzepa HS. Chem. Commun.  1997,  645 
    CrossrefGoogle Scholar
  • 9 Schlosser M. Michel D. Tetrahedron  1996,  52:  99 
    CrossrefGoogle Scholar
  • 10 Olsen JA. Banner DW. Seiler P. Obst-Sander U. D’Arcy A. Stihle M. Müller K. Diederich F. Angew. Chem. Int. Ed.  2003,  42:  2507 ; Angew. Chem. 2003, 115, 2611
    CrossrefGoogle Scholar
  • 11 Olsen J. Seiler P. Wagner B. Fisher H. Tschopp T. Obst-Sander U. Banner DW. Kansy M. Müller K. Diederich F. Org. Biomol. Chem.  2004,  2:  1339 
    CrossrefGoogle Scholar
  • 12 Meyer EA. Castellano RK. Diederich F. Angew. Chem. Int. Ed.  2003,  42:  1210 ; Angew. Chem. 2003, 115, 1244
    CrossrefPubMedGoogle Scholar
  • 13 Paulini R. Müller K. Diederich F. Angew. Chem. Int. Ed.  2005,  44:  1788 ; Angew. Chem. 2005, 117, 1820
    CrossrefGoogle Scholar
  • 14 Haufe G. Kröger S. Amino Acids  1996,  11:  409 
    CrossrefGoogle Scholar
  • 15a Nikolova GS. Zhang L. Chen X. Chi L. Haufe G. Colloids Surf. A  2008,  317:  414 
    Google Scholar
  • 15b Chen X. Wiehle S. Weygand M. Brezesinski G. Klenz U. Galla H.-J. Fuchs H. Haufe G. Chi L. J. Phys. Chem. B  2005,  109:  19866 
    Google Scholar
  • 15c Chen X. Wiehle S. Chi L. Mück-Lichtenfeld C. Rudert R. Vollhardt D. Fuchs H. Haufe G. Langmuir  2005,  21:  3376 
    Google Scholar
  • 16a Steffens S. Höweler U. Jödicke T. Oldendorf J. Rudert R. Haufe G. Galla H.-J. Langmuir  2007,  23:  1880 
    Google Scholar
  • 16b Steffens S. Oldendorf J. Haufe G. Galla H.-J. Langmuir  2006,  22:  1428 
    Google Scholar
  • 17 Nikolova GS. Haufe G. Beilstein J. Org. Chem.  2008,  4(12):  1 
    Google Scholar
  • 18a Koroniak K. Haufe G. Synthesis  2010,  498 
    Google Scholar
  • 18b Oldendorf J. Haufe G. Eur. J. Org. Chem.  2006,  4463 
    Google Scholar