A new approach to the synthesis of lysophospholipids: Preparation of lysophosphatidic acid and lysophosphatidylcholine from p-nitrophenyl glycerate

Tetrahedron Letters

Volumn 45, Issue 39, 2004, Pages 7371-7373

  Rosseto, Renato ^a   Bibak, Niloufar ^a   Hajdu, Joseph ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

Chemoselective reduction; Lysophosphatidic acid; Lysophosphatidylcholine synthesis; p Nitrophenyl glycerate

Indexed keywords

4 NITROPHENYLGLYCERATE; ESTER; GLYCERIC ACID; LYSOPHOSPHATIDIC ACID; LYSOPHOSPHATIDYLCHOLINE; LYSOPHOSPHOLIPID; PHENYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; MOLECULE; REDUCTION; STEREOSPECIFICITY; SYNTHESIS;

EID: 4444383384     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.07.161     Document Type: Article

References (25)

1. W.H. Moolenaar J. Biol. Chem. 270 1995 12949 12952
2. W.H. Moolenaar Exp. Cell. Res. 253 1999 230 238
3. G. Tigyi, and A.L. Parrill Prog. Lipid Res. 42 2003 498 526
4. E.J. Goetzl, and S. An FASEB J. 12 1998 1589 1598
5. L. McPhail D.E. Vance J.E. Vance Biochemistry of Lipids, Lipoproteins and Membranes 4th ed. 2002 Elsevier Science Amsterdam 315 340
6. T. Sugiura, A. Tokumura, L. Gregory, T. Nouchi, S.T. Weintraub, and D.J. Hanahan Arch. Biochem. Biophys. 311 1994 358 368
7. A. Tokumura, K. Fukuzawa, J. Isobe, and H. Tsukatani Biochem. Biophys. Res. Commun. 99 1981 391 398
8. A. Tokumura, K. Fukuzawa, and H. Tsukatani J. Pharm. Pharmacol. 34 1982 514 516
9. A. Tokumura, K. Fukuzawa, Y. Akamatsu, and H. Tsukatani Lipids 13 1978 468 475
10. A. Tokumura Prog. Lipid Res. 34 1995 151 184
11. F. Imamura, T. Horai, M. Mukai, K. Shinkai, M. Sawada, and H. Akedo Biochem. Biophys. Res. Commun. 193 1993 497 503
12. J.C. Stam, F. Michiels, R.A. Van der Kammen, W.H. Moolenaar, and J.G. Collard EMBO J. 17 1998 4066 4074
13. A.B. Nixon, J.T. O'Flaherty, J.K. Salyer, and R.L. Wykle J. Biol. Chem. 274 1999 5469 5473
14. X. Fang, S. Gibson, M. Flower, T. Furui, R.C. Bast Jr., and J.B. Mills J. Biol. Chem. 272 1997 13683 13689
15. Y. Yuan, S.M. Schoenwaelder, H.H. Salem, and S.P. Jackson J. Biol. Chem. 271 1996 27090 27098
16. Y. Yuan, S.P. Jackson, H.H. Newnham, C.A. Mitchell, and H.H. Salem Blood 86 1995 4166 4174
17. G.K. Marathe, A.R. Silva, H.C. de Castro Faria Neto, L.W. Tjoelker, S.M. Prescott, G.A. Zimmerman, and T.M. McIntyre J. Lipid Res. 42 2001 1430 1437
18. K. Kuglyama, S. Kerns, J.D. Morrisett, R. Roberts, and P.D. Henry Nature 344 1990 160 162
19. J. Chevallier, N. Sakai, F. Robert, T. Kobayashi, J. Gruenberg, and S. Matile Org. Lett. 2 2000 1859 1861
20. A. Wang, R. Loo, Z. Chen, and E.A. Dennis J. Biol. Chem. 272 1997 22030 22036
21. N. Bibak, and J. Hajdu Tetrahedron. Lett. 44 2003 5875 5877
22. W. Srisiri, Y.S. Lee, and D.F. O'Brien Tetrahedron Lett. 36 1995 5911 5914
23. 2 mixture the reduction was slow, and the yield of the alcohol was low (∼30%): S. Takahashi, and L.A. Cohen J. Org. Chem. 35 1970 1505 1508
24. We have used a base-labile variant of the original phosphoramidite method in order to prevent cleavage of the sn-2-tetrahydropyranyl group: J.W. Perich, and R.B. Johns Tetrahedron Lett. 29 1988 2369 2372
25. F.S. Roodsari, D. Wu, G.S. Pum, and J. Hajdu J. Org. Chem. 64 1999 7727 7737