Synthesis of tritium labelled phosphonate analogues of sphinganine-1-phosphate

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 39, Issue 5, 1997, Pages 441-451

  Schick, Andreas ^a   Schwarzmann, Günter ^a   Kolter, Thomas ^a   Sandhoff, Konrad ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Lipid second messenger; Signalling; Sphinganine 1 phosphate; Sphingolipids; Sphingosine 1 phosphate

Indexed keywords

% REDUCTIONS; LIPID SECOND MESSENGER; PHOSPHONATES; SIGNALING; SPHINGANINE; SPHINGANINE-1-PHOSPHATE; SPHINGOLIPIDS; SPHINGOSINE 1 PHOSPHATES; TRIPLE BONDS; TRITIATION;

TRITIUM;

PHOSPHONIC ACID DERIVATIVE; SPHINGOLIPID; TRITIUM;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; ISOTOPE LABELING; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RADIOCHEMISTRY;

TRITIUM;

EID: 0030952718     PISSN: 03624803     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1344(199705)39:5<441::AID-JLCR988>3.0.CO;2-D     Document Type: Article

References (37)

1. Sweeley C.C., in "Biochemistry of Lipids and Membranes", Vance D. E. and Vance J. E.-Eds., Elsevier, Amsterdam, 327 (1991).
2. a) Hakomori S. - Trends Biochem. Sci. 9: 453 (1984)
3. b) Hakomori S. and Igarashi Y. - Adv. Lipid Res. 25: 147 (1993)
4. c) Hakomori S. - Biochem. Soc. Trans. 21: 583 (1993)
5. Rother J., van Echten G., Schwarzmann G. and Sandhoff K. - Biochem. Biophys. Res. Commun. 189: 14 (1992)
6. a) Hannun Y.A., Loomis C.R., Merrill A.H. and Bell R.M. - J. Biol. Chem. 261: 12604 (1986)
7. b) Hannun Y.A. and Bell R.M. - Science. 235: 670 (1987)
8. a) Hirschberg C.B., Kisic A. and Schroepfer G.J. - J. Biol. Chem. 254: 3084 (1970)
9. b) Stoffel W., Hellenbroich B. and Heiman G. - Hoppe-Seyler's Z. Physiol. Chem. 354: 1311 (1973)
10. c) Keenan R.W. and Okabe K. - Biochemistry. 7: 2696 (1968)
11. d) Stoffel W., Assman G. and Binczeck E. - Hoppe-Seyler's Z. Physiol. Chem. 351: 635 (1970)
12. e) Louie D.D., Kisic A. and Schroepfer G.J. - J. Biol. Chem. 251: 4557 (1976)
13. Buehrer B.M. and Bell R.M. - Adv. Lipid Res. 26: 59 (1993)
14. a) Olivera A. and Spiegel S. - Nature. 365: 557 (1993)
15. b) Zhang H., Desai N.N., Olivera A., Seki T., Brooker G. and Spiegel S. - J. Cell Biol. 114: 155 (1991)
16. Mattie M., Brooker G. and Spiegel S. - J. Biol. Chem. 269: 3181 (1994)
17. Gosh T.K., Bian J. and Gill D.L. - J. Biol. Chem. 269: 22628 (1994)
18. Kim S., Lakhani V., Costa D.J. Sharara A.I., Fitz J.G., Huang L.W., Peters K.G. and Kindman L.A. - J. Biol. Chem. 270: 5266 (1995)
19. Goodemote K.A., Matties M.E., Berger A. and Spiegel S. - J. Biol. Chem. 270: 10272 (1995)
20. Van Koppen C.J., Meyer zu Heringdorf D., Laser K.T., Zhang Ch. and Jakobs K.H., Bünemann M. and Pott L. - J. Biol. Chem. 271: 2082 (1996)
21. Stoffel W., Sticht G. and Le Kim D. - Hoppe-Seyler's Z. Physiol. Chem. 349: 1745 (1968)
22. Stoffel W., Bauer E. and Stahl J. - Hoppe-Seyler's Z. Physiol. Chem. 355: 61 (1973)
23. Shimojo T., Akino T., Miura Y. and Schroepher G.J. - Biochim. Biophys. Acta 431: 433 (1976)
24. Van Veldhoven P.P. and Mannaerts G.P. - Biochem. J. 299: 597 (1994)
25. Schick A., Kolter T., Giannis A. and Sandhoff K. - Tetrahedron 51: 11207 (1995)
26. Schick A., Kolter T., Giannis A. and Sandhoff K. - Tetrahedron 52: 2945 (1996)
27. Schick A., van-Echten-Deckert G. and Sandhoff K., manuscript in preparation
28. Schwarzmann G. - Biochim. Biophys. Acta 529: 106 (1978)
29. Wilzbach K.E. - J. Am. Chem. Soc. 72: 1013 (1957)
30. Brady R.O., Gal A.E., Bradley R.M. and Märtensson E. - J. Biol. Chem. 242: 1021 (1967)
31. Crawhall J.C. and Smyth D.G. - Biochem. J. 69: 280 (1950)
32. Gatt S. and Rapport M.M. - Biochem. J. 101: 680 (1966)
33. Seyama Y., Yamakawa T. and Komai T. - J. Biochem. Tokyo 64: 487 (1968)
34. DiCesare J.L. and Rapport M.M. - Chem. Phys. Lipids 13: 447 (1974)
35. Iwamori M., Moser H.W. and Kishimoto Y. - J. Lipid Res. 16: 332 (1975)
36. Ghidoni R., Sonnino S., Masserini M., Orlando P. and Tettamanti G. - J. Lipid. Res. 22: 1286 (1981)
37. Sonnino S., Marco N. and Chigorno V. - Glycobiology 6: 479 (1996)