Syntheses of polymerizable monoacylglycerols and 1,2-diacyl-sn-glycerols

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 5911-5915

  Srisiri, Warunee ^a   Lamparski, Henry G ^a   O'Brien, David F ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCEROL DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PHASE TRANSITION; POLYMERIZATION;

EID: 0029827164     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960010b     Document Type: Article

References (38)

1. O'Brien, D. F. Trends Polym. Sci. 1994, 2, 183-188.
2. O'Brien, D. F.; Ramaswami, V. Encyclopedia of Polymer Science and Engineering, 2nd ed.; Wiley: New York, 1989; pp 108-135.
3. (a) Ringsdorf, H.: Schlarb, B.; Venzmer, J. Angew. Chem., Int. Ed. Engl. 1988, 27, 113-158.
4. (b) Singh, A.; Schnur, J. M. Polymerizable Phospholipids. In Phospholipids Handbook; Cevc, G., Ed.; Marcel Dekker: New York, 1993; pp 233-291.
5. Lindblom, G.; Rilfors, L. Biochim. Biophys. Acta 1989, 988, 221-256.
6. Seddon, J. M. Biochim. Biophys. Acta 1990, 1031, 1-69.
7. Tate, M. W.; Eikenberry, E. F.; Turner, D. C.; Shyamsunder, E.; Gruner, S. M. Chem. Phys. Lipids 1991, 57, 147-164.
8. Lee, Y.-S.; Srisiri, W.; Devanathan, S.; O'Brien, D. F. Submitted for publication.
9. Lee, Y.-S.; Yang, J.; Sisson, T. M.; Frankel, D. A.; Gleeson, J. T.; Aksay, E.; Keller, S. L.; Gruner, S. M.; O'Brien, D. F. J. Am. Chem. Soc. 1995, 117, 5573-5578.
10. Hyde, S.; Andersson, S.; Ericsson, B.; Larsson, K. Z. Kristallogr. 1984, 168, 213-219.
11. Briggs, J.; Caffrey, M. Biophys. J. 1994, 66, 573-587.
12. Briggs, J.; Caffrey, M. Biophys. J. 1994, 67, 1594-1602.
13. Nilsson, A.; Holmgren, A.; Lindblom, G. Biochemistry 1991, 30, 2126-2133.
14. Tsuchida, E.; Hasegawa, E.; Kimura, N.; Hatashita, M.; Makino, E. Macromolecules 1992, 25, 207-212.
15. Lamparski, H. G.; O'Brien, D. F. Macromolecules 1995, 28, 1786-1794.
16. Martin, S. F.; Josey, J. A.; Wong, Y.-L.; Dean, D. W. J. Org. Chem. 1994, 59, 4805-4820.
17. Majerus, P. W.; Connolly, T. M.; Deckmyn, H.; Ross, T. E.; Ishii, H.; Bansal,U.S.; Wilson, D. B. Science 1986, 234, 1519-1526.
18. Berridge, M. J. Annu. Rev. Biochem. 1987, 56, 159-193.
19. Ohki, T.; Sekiya, T.; Yamauchi, T.; Nozawa, T. Biochim. Biophys. Acta 1982, 693, 341-350.
20. Ortiz, A.; Villalain, J.; Gomez-Fernandez, J. C. Biochemistry 1988, 27, 9030-9036.
21. Lopez-Garcia, F.; Villalain, J.; Gomez-Femandez, J. C.; Quinn, P. J. Biophys. J. 1995, 68, 558-566.
22. Siegel, D. P.; Banschbach, J.; Alford, D.; Ellens, H.; Lis, L. J.; Quinn, P. J.; Yeagle, P. L.; Bentz, J. Biochemistry 1989, 28, 3703-9.
23. Siegel, D. P.; Banschbach, J.; Yeagle, P. L. Biochemistry 1989, 28, 5010-5019.
24. Dorn, K.; Klingbiel, R. T.; Specht, D. P.; Tyminiski, P. N.; Ringsdorf, H.; O'Brien, D. F. J. Am. Chem. Soc. 1984, 106, 1627-1633.
25. Allen, C. F.; Kalm, K. J. Org. Synth. 1963, 4, 608-611.
26. Jung, M. E.; Lyster, M. A. J. Am. Chem. Soc. 1977, 99, 968-969.
27. Fetterly, L. C. Non-Stoichiometric Compounds; Mandelcorn, L., Ed.; Academic Press: New York, 1965; Chapter 8.
28. (a) Farina, N. Inclusion Compounds; Atword, J. L., et al., Eds.; Academic Press: New York, 1984; Vol. 2, p 69.
29. (b) Reference 27a, Vol. 3, p 297.
30. Smith, A. E. Acta. Crystallogr. 1952, 5, 224.
31. (a) Fieser, L. F. J. Chem. Educ. 1963, 457
32. (b) 1965, 42, 408.
33. Kadali, D. R.; Tereyak, A.; Fahey, D. A.; Small, D. M. Chem. Phys. Lipids 1990, 52, 163-175.
34. Pfeiffer, F. R.; Cohen, S. R.; Weisbach, J. A. J. Org. Chem. 1969, 34, 2795-2796.
35. Pfeiffer, F. R.; Miao, C. K.; Weisbach, J. A. J. Org. Chem. 1970, 35, 221-224.
36. Hebert, N.; Beck, A.; Lennox, R. B.; Just, G. J. Org. Chem. 1992, 57, 1777-1783.
37. Ponpipom, M. M.; Bugianesi, R. L. J. Lipid Res. 1980, 21, 336-339.
38. Quindon, Y.; Yoakim, C.; Morton, H. E. J. Org. Chem. 1984, 29, 3912-3920.