Synthesis of plasmalogen via 2,3-bis-O-(4'-methoxybenzyl)-sn-glycerol

Journal of the American Chemical Society

Volumn 121, Issue 4, 1999, Pages 662-668

  Qin, Donghui ^a   Byun, Hoe Sup ^a   Bittman, Robert ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 BIS O (4' METHOXYBENZYL)GLYCEROL; GLYCEROL DERIVATIVE; PLASMALOGEN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; DECOMPOSITION; HYDROGENATION; ISOMERISM; OXIDATION REDUCTION REACTION; PALMITOYLATION; REACTION ANALYSIS; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033518579     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja982837o     Document Type: Article

References (56)

1. (a) Klenk, E.; Debuch, H. In Progress in the Chemistry of Fats and Other Lipids; Holman, R. T., Lundberg, W. O., Malkin, T., Eds.; Pergamon: New York, 1963; pp 1-29.
2. (b) Horrocks, L. A.; Sharma, M. In Phospholipids; Hawthorne, J. N., Ansell, G. B., Eds.; Elsevier: Amsterdam, 1982; Vol. 4, pp 50-93.
3. (a) Gross, R. W. Biochemistry 1984, 23, 158-165.
4. (b) Gross, R. W. Biochemistry 1985, 24, 1662-1668.
5. Snipes, J.; Suter, U. In Cholesterol: Its Functions and Metabolism in Biology and Medicine; Subcellular Biochemistry; Bittman, R., Ed.; Plenum: New York, 1997; Vol. 28, pp 173-204.
6. (a) Glaser, P. E.; Gross, R. W. Biochemistry 1994, 33, 5805-5812.
7. (b) Lohner, K. Chem. Phys. Lipids 1996, 81, 67-184.
8. (a) Farooqui, A. A.; Yang, H.-C.; Horrocks, L. A. Brain Res. Rev. 1995, 21, 152-161.
9. (b) Portilla, D.; Creer, M. H. Kidney Int. 1995, 47, 1087-1094.
10. (c) Farooqui, A. A.; Rapoport, S. I.; Horrocks, L. A. Neurochem. Res. 1997, 22, 523-527.
11. (d) McHowat, J.; Liu, S.; Creer, M. H. Am. J. Physiol. 1998, 274, C1727-C1737.
12. Schedin, S.; Sindelar, P. J.; Pentchev, P.; Brunk, U.; Dallner, G. J. Biol. Chem. 1997, 272, 6245-6251.
13. (a) Farooqui, A. A.; Horrocks, L. A. Biochem. Soc. Trans. 1998, 26, 243-246.
14. (b) Ginsberg, L.; Xuereb, J. H.; Gershfeld, N. L. J. Neurochem. 1998, 70, 2533-2538.
15. Perichon, R.; Moser, A. B.; Wallace, W. C.; Cunningham, S. C.; Roth, G. S.; Moser, H. W. Biochem. Biophys. Res. Commun. 1998, 248, 57-61.
16. (a) Paltauf, F. Chem. Phys. Lipids 1994, 74, 101-139.
17. (b) Bräutigam, C.; Engelmann, B.; Reiss, D.; Reinhardt, U.; Thiery, J.; Richter, W. O.; Brosche, T. Atherosclerosis 1996, 119, 77-88.
18. (c) Hofer, G.; Lichtenberg, D.; Kostner, G. M.; Hermetter, A. Clin. Biochem. 1996, 29, 445-450.
19. (d) Jira, W.; Spiteller, G. Chem. Phys. Lipids 1996, 79, 95-100.
20. Mandel, H.; Sharf, R.; Berant, M.; Wanders, R. J. A.; Vreken, P.; Aviram, M. Biochem. Biophys. Res. Commun. 1998, 250, 369-373.
21. For a review of the early literature, see: (a) Rosenthal, A. F. Methods Enzymol. 1975, 35, 429-529. (b) Paltauf, F. In Ether Lipids: Biochemical and Biomedical Aspects; Mangold, H. K., Paltauf, F., Eds.; Academic: New York, 1983; pp 49-84.
22. For a review of the early literature, see: (a) Rosenthal, A. F. Methods Enzymol. 1975, 35, 429-529. (b) Paltauf, F. In Ether Lipids: Biochemical and Biomedical Aspects; Mangold, H. K., Paltauf, F., Eds.; Academic: New York, 1983; pp 49-84.
23. For dehydrohalogenation of 1′- or 2′-halo-1-alkoxy glyceryl ethers and dehalogenation of 1′,2′-dichloroalkoxy glyceryl ethers (principally glycerol 1,2-cyclic carbonates), see: (a) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Zh. Org. Khim. 1977, 13, 703-709; Chem. Abstr. 1977, 87, 38790s. (b) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Bioorg. Khim. 1977, 3, 1362-1369; Chem. Abstr. 1977, 88, 37184f. (c) Titov, V. I.; Serebrennikov, G. A.; Preobrazhenskii, N, A. Zh. Org. Khim. 1970, 6, 1154-1159; Chem. Abstr. 1970, 73, 65983z. (d) Pfaendler, H. R.; Müller, F. X. Synthesis 1992, 350-352.
24. For dehydrohalogenation of 1′- or 2′-halo-1-alkoxy glyceryl ethers and dehalogenation of 1′,2′-dichloroalkoxy glyceryl ethers (principally glycerol 1,2-cyclic carbonates), see: (a) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Zh. Org. Khim. 1977, 13, 703-709; Chem. Abstr. 1977, 87, 38790s. (b) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Bioorg. Khim. 1977, 3, 1362-1369; Chem. Abstr. 1977, 88, 37184f. (c) Titov, V. I.; Serebrennikov, G. A.; Preobrazhenskii, N, A. Zh. Org. Khim. 1970, 6, 1154-1159; Chem. Abstr. 1970, 73, 65983z. (d) Pfaendler, H. R.; Müller, F. X. Synthesis 1992, 350-352.
25. For dehydrohalogenation of 1′- or 2′-halo-1-alkoxy glyceryl ethers and dehalogenation of 1′,2′-dichloroalkoxy glyceryl ethers (principally glycerol 1,2-cyclic carbonates), see: (a) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Zh. Org. Khim. 1977, 13, 703-709; Chem. Abstr. 1977, 87, 38790s. (b) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Bioorg. Khim. 1977, 3, 1362-1369; Chem. Abstr. 1977, 88, 37184f. (c) Titov, V. I.; Serebrennikov, G. A.; Preobrazhenskii, N, A. Zh. Org. Khim. 1970, 6, 1154-1159; Chem. Abstr. 1970, 73, 65983z. (d) Pfaendler, H. R.; Müller, F. X. Synthesis 1992, 350-352.
26. For dehydrohalogenation of 1′- or 2′-halo-1-alkoxy glyceryl ethers and dehalogenation of 1′,2′-dichloroalkoxy glyceryl ethers (principally glycerol 1,2-cyclic carbonates), see: (a) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Zh. Org. Khim. 1977, 13, 703-709; Chem. Abstr. 1977, 87, 38790s. (b) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Bioorg. Khim. 1977, 3, 1362-1369; Chem. Abstr. 1977, 88, 37184f. (c) Titov, V. I.; Serebrennikov, G. A.; Preobrazhenskii, N, A. Zh. Org. Khim. 1970, 6, 1154-1159; Chem. Abstr. 1970, 73, 65983z. (d) Pfaendler, H. R.; Müller, F. X. Synthesis 1992, 350-352.
27. For dehydrohalogenation of 1′- or 2′-halo-1-alkoxy glyceryl ethers and dehalogenation of 1′,2′-dichloroalkoxy glyceryl ethers (principally glycerol 1,2-cyclic carbonates), see: (a) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Zh. Org. Khim. 1977, 13, 703-709; Chem. Abstr. 1977, 87, 38790s. (b) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Bioorg. Khim. 1977, 3, 1362-1369; Chem. Abstr. 1977, 88, 37184f. (c) Titov, V. I.; Serebrennikov, G. A.; Preobrazhenskii, N, A. Zh. Org. Khim. 1970, 6, 1154-1159; Chem. Abstr. 1970, 73, 65983z. (d) Pfaendler, H. R.; Müller, F. X. Synthesis 1992, 350-352.
28. For dehydrohalogenation of 1′- or 2′-halo-1-alkoxy glyceryl ethers and dehalogenation of 1′,2′-dichloroalkoxy glyceryl ethers (principally glycerol 1,2-cyclic carbonates), see: (a) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Zh. Org. Khim. 1977, 13, 703-709; Chem. Abstr. 1977, 87, 38790s. (b) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Bioorg. Khim. 1977, 3, 1362-1369; Chem. Abstr. 1977, 88, 37184f. (c) Titov, V. I.; Serebrennikov, G. A.; Preobrazhenskii, N, A. Zh. Org. Khim. 1970, 6, 1154-1159; Chem. Abstr. 1970, 73, 65983z. (d) Pfaendler, H. R.; Müller, F. X. Synthesis 1992, 350-352.
29. For dehydrohalogenation of 1′- or 2′-halo-1-alkoxy glyceryl ethers and dehalogenation of 1′,2′-dichloroalkoxy glyceryl ethers (principally glycerol 1,2-cyclic carbonates), see: (a) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Zh. Org. Khim. 1977, 13, 703-709; Chem. Abstr. 1977, 87, 38790s. (b) Chebyshev, A. V.; Serebrennikova, G. A.; Evstigneeva, R. P. Bioorg. Khim. 1977, 3, 1362-1369; Chem. Abstr. 1977, 88, 37184f. (c) Titov, V. I.; Serebrennikov, G. A.; Preobrazhenskii, N, A. Zh. Org. Khim. 1970, 6, 1154-1159; Chem. Abstr. 1970, 73, 65983z. (d) Pfaendler, H. R.; Müller, F. X. Synthesis 1992, 350-352.
30. (a) Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668-2670.
31. (b) Okazoe, T.; Takai, K.; Oshima, K.; Utimoto, K. J. Org. Chem. 1987, 52, 4412-4414.
32. Rui, Y.; Thompson, D. H. J. Org. Chem. 1994, 59, 5758-5762.
33. (a) Charbonnier, F.; Moyano, A.; Greene, A. E. J. Org. Chem. 1987, 52, 2303-2306.
34. (b) Rui, Y.; Thompson, D. H. Chem. Eur. J. 1996, 2, 1505-1508.
35. Byun, H.-S.; Kumai, E. R.; Bittman, R. J. Org. Chem. 1994, 59, 2630-2633.
36. Betezovskaya, M. V.; Sarycheva, I. K.; Preobrazhenskii, N. A. Zh. Obshch. Khim. 1964, 34, 543-545; Chem. Abstr. 1964, 60, 11886f.
37. Betezovskaya, M. V.; Sarycheva, I. K.; Preobrazhenskii, N. A. Zh. Obshch. Khim. 1964, 34, 543-545; Chem. Abstr. 1964, 60, 11886f.
38. Chacko, G. K.; Schilling, K.; Perkins, E. G. J. Org. Chem. 1967, 32, 3698-3700.
39. Moyano, A.; Charbonnier, F.; Greene, A. E. J. Org. Chem. 1987, 52, 2919-2922.
40. Mangold, H. K. Angew. Chem., Intl. Ed. Engl. 1979, 18, 493-503.
41. (a) Lindlar, H. Helv. Chim. Acta 1952, 35, 446-450.
42. (b) McEwen, A. B.; Guttieri, M. J.; Maier, W. F.; Laine, R. M.; Shvo, Y. J. Org. Chem. 1983, 48, 4436-4438.
43. (a) Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885-888.
44. (b) Buckle, D. R. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone. In Encyclopedia of Reagents for Organic Synthesis; Raquette, L. A., Ed.; Wiley: Chichester, 1995; Vol. 3, pp 1699-1704.
45. For reviews of acylation of lipid hydroxy groups, see: (a) Radhakrishnan, R.; Robson, R. J.; Takagaki, Y.; Khorana, H. G. Methods Enzymol. 1981, 72, 408-435. (b) Bittman, R. In Phospholipids Handbook; Cevc, G., Ed.; Marcel Dekker: New York, 1993; pp 141-232.
46. For reviews of acylation of lipid hydroxy groups, see: (a) Radhakrishnan, R.; Robson, R. J.; Takagaki, Y.; Khorana, H. G. Methods Enzymol. 1981, 72, 408-435. (b) Bittman, R. In Phospholipids Handbook; Cevc, G., Ed.; Marcel Dekker: New York, 1993; pp 141-232.
47. Vilchèze, C.; Bittman, R. J. Lipid Res. 1994, 35, 734-738.
48. The Z/E ratio is highly sensitive to the concentrations of substrate and catalyst. This ratio was obtained by using 1.0 g (1.72 mmol) of 14, 100 mg of Lindlar catalyst, and 50 μL of quinoline in 30 mL of hexane/ EtOAc 1:1; reaction time, 2 h. It should be noted that Z/E ratios higher than 66:1 were obtained when shorter reaction times were used. Under these conditions, however, unreacted alkyne was sometimes present, and when the reaction mixture was subjected to another cycle of Lindlar reduction, the Z/E ratio of 15 was reduced.
49. Direct introduction of a phosphocholine group at the sn-3 position of diol 2 could not be achieved without obtaining a substantial amount of byproduct from reaction at the sn-2 hydroxy group. However, for selective phosphitylation of other glycerol diol derivatives, see: (a) Erukulla, R. K.; Byun, H.-S.; Bittman, R. Tetrahedron Lett. 1994, 35, 5783-5784. (b) Byun, H.-S.; Erukulla, R. K.; Bittman, R. J. Org. Chem. 1994, 59, 6495-6498.
50. Direct introduction of a phosphocholine group at the sn-3 position of diol 2 could not be achieved without obtaining a substantial amount of byproduct from reaction at the sn-2 hydroxy group. However, for selective phosphitylation of other glycerol diol derivatives, see: (a) Erukulla, R. K.; Byun, H.-S.; Bittman, R. Tetrahedron Lett. 1994, 35, 5783-5784. (b) Byun, H.-S.; Erukulla, R. K.; Bittman, R. J. Org. Chem. 1994, 59, 6495-6498.
51. The yield of palmitoylation using palmitoyl chloride and pyridine was lower (85%), probably because the pyridinium chloride formed during the reaction caused some decomposition of enol ether 16.
52. For reviews about the use of this cyclic phosphochloridate for phosphorylation of glycerol derivatives, see: (a) Reference 23b. (b) Bittman, R. In Lipid Synthesis and Manufacture: Gunstone, F. D., Ed.; Sheffield Academic Press: Sheffield, U. K.; CRC Press: Boca Raton, FL, 1998: pp 185-207.
53. For reviews about the use of this cyclic phosphochloridate for phosphorylation of glycerol derivatives, see: (a) Reference 23b. (b) Bittman, R. In Lipid Synthesis and Manufacture: Gunstone, F. D., Ed.; Sheffield Academic Press: Sheffield, U. K.; CRC Press: Boca Raton, FL, 1998: pp 185-207.
54. 15b
55. DeMedeiros, E. F.; Herbert, J. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1991, 2725-2730.
56. Hébert, N.; Beck, A.; Lennox, R. B.; Just, G. J. Org. Chem. 1992, 57, 1777-1783.