A new approach to the synthesis of lysophosphatidylcholines and related derivatives

Tetrahedron Letters

Volumn 44, Issue 31, 2003, Pages 5875-5877

  Bibak, Niloufar ^a   Hajdu, Joseph ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

Lysophosphatidylcholine synthesis; Methyl glycerate; Orthogonal O protection

Indexed keywords

CARBONIC ACID DERIVATIVE; ETHER DERIVATIVE; GLYCERIC ACID; HYDROXYL GROUP; LYSOPHOSPHATIDYLCHOLINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GEL CHROMATOGRAPHY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0038645672     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01419-9     Document Type: Article

References (20)

1. Paltauf F., Hermetter A. Prog. Lipid Res. 33:1994;254.
2. Hajdu J. Recent Res. Dev. Lipid Res. 3:1999;165.
3. Bradshaw J.P., Bushby R.J., Giles C.C.D., Saunders M.R. Biochemistry. 38:1999;8393.
4. Dowhan W., Bogdanov M. Vance D.E., Vance J.E. Biochemistry of Lipids, Lipoproteins and Membranes. 4th ed:2002;1-35 Elsevier Science, Amsterdam.
5. Muresan A.S., Diamant H., Lee K.Y. J. Am. Chem. Soc. 123:2001;6951.
6. Davies S.M.A., Epand R.M., Kraayenhof R., Cornell R.B. Biochemistry. 40:2001;10522.
7. Thirugnanam S., Topham M.K., Epand R.M. Biochemistry. 40:2001;10607.
8. White S.H., Ladokhin A.S., Jayasinghe S., Hristova K. J. Biol. Chem. 276:2001;32395.
9. Morash S.C., Cook H.W., Spence M.W. Biochim. Biophys. Acta. 1004:1989;221.
10. Wang A., Loo R., Chen Z., Dennis E.A. J. Biol. Chem. 272:1997;22030.
11. McPhail L. Vance D.E., Vance J.E. Biochemistry of Lipids, Lipoproteins and Membranes. 4th ed:2002;315-340 Elsevier Science, Amsterdam.
12. Vogler W.R., Olson A.C., Shoji M., Kiss Z., Kuo J.F. Kabara J.J. The Pharmacological Effects of Lipids. III:1989;314-329 American Oil Chemists' Society (AOCS), Lauricidin, Galena, IL.
13. Hla T., Lee M.J., Ancellin N., Paik J.M., Kluk M.J. Science. 294:2001;1875.
14. Goetzl E.J. Prostaglandins Other Lipids Med. 64:2001;11.
15. Bittman R. Cevc G. Phospholipid Handbook. 1993;141-232 Marcel Dekker, New York.
16. Srisiri W., Lee Y.-S., O'Brien D.F. Tetrahedron Lett. 36:1995;5911.
17. Hajdu J., Smith G.M. J. Am. Chem. Soc. 103:1981;6192.
18. We have obtained preliminary evidence that the same series of reactions can also be carried out using a series of substituted fatty acid derivatives. Along these lines, carboxylic acids functionalized at the chain terminal position with fluorescent reporter groups such as coumarin-343, and metal binding tetraazacyclododecyl groups have been incorporated into the synthetic phospholipid compounds.
19. 15.
20. Balet C., Clingman K.A., Hajdu J. Biochem. Biophys. Res. Commun. 150:1988;561.