Skip to main content
Log in

Ceramide-1-phosphate sugars: new types of glycophospholipids

  • Glycoconjugate Journal
  • Published:
Glycoconjugate Journal Aims and scope Submit manuscript

Abstract

Ceramide-1-phosphate sugars were synthesized by direct glycosyl phosphite/phosphate andO-glycosyl trichloroacetimidate/phosphate exchange reactions, respectively. Thus, ceramide-1-O-phosphoric acid 5 gave with sialyl phosphite1 as sialyl donor directly β-linked sialyl phosphate6; deprotection afforded the corresponding glycophospholipid ceramide-1-phosphateN-acetylneuraminate7. Similarly, fromO-glucosyl- andO-galactosyltrichloroacetimidate10 and13 with phosphoric acid derivative5 glycosyl ceramide-1-phosphate sugars12 and15, respectively, were obtained.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Ichikawa Y, Look GC, Wong C-H (1992)Anal Biochem 202: 215–38.

    Google Scholar 

  2. Westheimer FM (1987)Science 235: 1173–78.

    Google Scholar 

  3. Ferguson MAJ, Williams AF (1988)Annu Rev Biochem 57: 285–320.

    Google Scholar 

  4. Mayer TG, Kratzer B, Schmidt RR (1994)Angew Chem 106: 2289–93;Angew Chem Int Ed Engl 33: 2177–81; and references therein.

    Google Scholar 

  5. Van Heijenoort J, van Heijenoort Y, Welzel P (1988) InAntibiotic Inhibition of Bacterial Cell Wall Surface Assembly and Function (Actor P, Daneo-Moore L, Higgins ML, Satton MRJ, Shockman GD, eds) pp. 547–549. Washington: American Society for Microbiology.

    Google Scholar 

  6. Lüning J, Markus A, Welzel P (1994)Tetrahedron Lett 35: 1859–62; and references therein.

    Google Scholar 

  7. Martin TJ (1994)Dissertation, Univ. Konstanz.

  8. Dufner G, investigations for the PhD Thesis.

  9. Schmidt RR, Stumpp M (1984)Liebigs Ann Chem 680–91.

  10. Verheij HM, Smith PF, Bonsen PPM, van Deenen LLM (1970)Biochim Biophys Acta 218: 97–101.

    Google Scholar 

  11. Volkova LV, Luchinskaya MG, Karimova NM, Evstigneeva RP (1972)Zh Obshch Khim 42: 1405–8 [English translation (1972)J Gen Chem USSR 42: 1397–1400].

    Google Scholar 

  12. Martin TJ, Schmidt RR (1993)Tetrahedron Lett 34: 1765–68.

    Google Scholar 

  13. Martin TJ, Braun H, Schmidt RR (1994)Bioorg Med Chem 2: 1203–8.

    Google Scholar 

  14. Kratzer B, Schmidt RR (1995)Liebigs Ann Chem 957–63.

  15. Martin TJ, Schmidt RR (1992)Tetrahedron Lett 33: 6123–26.

    Google Scholar 

  16. Martin TJ, Brescello R, Toepfer A, Schmidt RR (1993)Glycoconjugate J 10: 16–25.

    Google Scholar 

  17. Kläger R (1982)Dissertation, Univ. Konstanz.

  18. Bannwarth W, Trzeciak A (1987)Helv Chim Acta 70: 175–86.

    Google Scholar 

  19. Beaucage SL, Iyer RP (1993)Tetrahedron 49: 10441–49.

    Google Scholar 

  20. Chao H-G, Bernatowicz MS, Klimas CE, Matsueda GR (1993)Tetrahedron Lett 34: 3370–80.

    Google Scholar 

  21. Schmidt RR (1986)Angew Chem 98: 213–36;Angew Chem Int Ed Engl 25: 212–35.

    Google Scholar 

  22. Hoch M, Heinz E, Schmidt RR (1989)Carbohydr Res 191: 21–28.

    Google Scholar 

  23. Schmidt RR, Wegmann B, Jung K-H (1991)Liebigs Ann Chem 121–24.

  24. Schmidt RR, Michel J, Roos M (1984)Liebigs Ann Chem 1343–57.

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Martin, T.J., Dufner, G., Kratzer, B. et al. Ceramide-1-phosphate sugars: new types of glycophospholipids. Glycoconjugate J 13, 547–553 (1996). https://doi.org/10.1007/BF00731442

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00731442

Keywords

Navigation