On the synthesis of platelet-activating factor via acetylation of 1-alkyl-sn-glycero-3-phosphocholine. Formation of structural isomer of PAF in the presence of bases

Chemistry and Physics of Lipids

Volumn 81, Issue 1, 1996, Pages 35-43

  Chupin, V V ^a   Ostapenko, O V ^a   Klykov, V N ^a   Anikin, M V ^a   Screbrennikova, G A ^a  

^a MV Lomonosor State Acad of Fine   (Russian Federation)

Author keywords

Acetylation; Lyso platelet activating factor; Platelet activating factor; Positional isomer

Indexed keywords

1 O ALKYLGLYCERO 3 PHOSPHORYLCHOLINE; ACETIC ANHYDRIDE; BASE; GLYCEROPHOSPHORYLCHOLINE DERIVATIVE; THROMBOCYTE ACTIVATING FACTOR;

ACETYLATION; ARTICLE; CATALYSIS; ISOMER; PRIORITY JOURNAL; SYNTHESIS;

EID: 0030591478     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/0009-3084(96)02530-3     Document Type: Article

References (30)

1. [1] Platelet-Activating Factor and Related Lipid Mediators (1987) in: F. Snyder (Ed.), Plenum Press, New York, London.
2. [2] P. Braquet, L. Touqui, T.Y. Shen and B.B. Vargaftig (1987) Pharmacol. Rev. 39, 97-145.
3. [3] C.A. Demopoulos, N.R. Pinckard and D.J. Hanahan (1979) J. Biol. Chem. 254, 9355-9358.
4. [4] J. Benveniste, M. Tence, P. Varenne, J. Bidault, C. Boullet and J. Polonsky (1979) C.R. Acad. Sci. Paris 289. 1037-1040.
5. [5] M. Ohno, K. Fujita, H. Nakai, S. Kobayashi, K. Inoue and S. Nojima (1985) Chem. Pharm. Bull. 33, 572-582.
6. [6] K. Fujita, H. Nakai, S. Kobayashi, K. Inoue, S. Nojima and M. Ohno (1982) Tetrahedron Lett. 23, 3507-3510.
7. [7] C.A.A. van Boeckel, G.A. van der Marel, P. Westerduin and J.H. van Boom (1982) Synthesis 5, 399-402.
8. [8] J.-J. Godfroid, F. Heymans, E. Michel, C. Redeuilh, E. Steiner and J. Benveniste (1980) FEBS Lett. 116, 161-164.
9. [9] H.-P. Kertscher and G. Ostermann (1986) Pharmazie 41, 596.
10. [10] A. Kumar and V. Bhakuni (1993) Tetrahedron Lett. 34, 3463-3466.
11. [11] J.R. Surles, R.L. Wykle, J.T. O'Flaherty, W.L. Salzer, M.J. Thomas, F. Snyder and C. Piantadosi (1985) J. Med. Chem. 28, 73-78.
12. [12] T. Tsuri and S. Kamata (1985) Tetrahedron Lett. 26, 5195-5198.
13. [13] P.N. Guivisdalsky and R. Bittman (1989) J. Org. Chem. 54, 4643-4648.
14. [14] N. Nakamura, H. Miyazaki, N. Ohkawa, T. Oshima and H. Koike (1990) Tetrahedron Lett. 31, 699-702.
15. [15] F. Heymans, E. Michel, M.-C. Borrel, B. Wichrowski, J.-J. Godfroid, O. Convert, E. Coeffier, M. Tence and J. Benveniste (1981) Biochim. Biophys. Acta 666, 230-237.
16. [16] G. Hirth and R. Barner (1982) Helv. Chim. Acta 65, 1059-1084.
17. [17] P. Bett-Bobillo, A. Bienvenue, C. Broquet and L. Maurin (1985) Chem. Phys. Lipids 37, 215-226.
18. [18] V.V. Chupin, O.V. Ostapenko, V.N. Klykov, M.V. Anikin, and G.A. Serebrennikova (1993) Bioorgan. Khim. 19, 1111-1121.
19. [19] B. Palameta and M. Kates (1966) Biochemistry 5, 618-625.
20. [20] A.F. Rosenthal (1966) J. Lipid Res. 7, 779-785.
21. [21] J.C. Dittmer and R.L. Lester (1964) J. Lipid Res. 5, 126-127.
22. [22] H. Brockerhoff and N.K.N. Ayengar (1979) Lipids 14, 88-89.
23. [23] M.P. Murari, R. Murari, S. Parthasarathy, C.A. Guy, V.V. Kumar and B. Malewicz (1990) Lipids 25, 606-612.
24. [24] A. Pluckthun and E.A. Dennis (1982) Biochemistry 21, 1743-1750.
25. [25] M. Tence, E. Coeffier, J. Polonsky and J. Benveniste (1983) Biochim. Biophys. Acta 755, 526-530.
26. [26] R. Kumar, S.T. Weintraub, L.M. McManus, R.N. Pinckard and D.J. Hanahan (1984) J. Lipid Res. 25, 198-208.
27. [27] L.L.M. Van Deenen and G.H. de Haas (1963) Biochim. Biophys. Acta 70, 538-553.
28. [28] G.H. De Haas and L.L.M. van Deenen (1964) Biochim. Biophys. Acta 84, 469-471.
29. [29] G.H. De Haas and L.L.M. van Deenen (1965) Biochim. Biophys. Acta 106, 315-325.
30. [30] V.V. Chupin, E.V. Malina, I.V. Revenko, I.A. Vasilenko, G. A. Screbrennikova and R.P. Evstigneeva (1984) Bioorg. Khim. 10, 970-974.