Synthesis of Benzophenone-Containing Analogues of Phosphatidylcholine

Journal of Organic Chemistry

Volumn 69, Issue 8, 2004, Pages 2693-2702

  Wang, Pingzhen ^a   Blank, David H ^a   Spencer, Thomas A ^a  

^a Dartmouth College   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CARBOXYLIC ACIDS; CHOLESTEROL; ETHERS; HYDROGENATION; PHOSPHOLIPIDS; SYNTHESIS (CHEMICAL);

ALKYL CHAINS; PHOTOACTIVABLE ANALOGUES;

KETONES;

BENZOPHENONE DERIVATIVE; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID DERIVATIVE;

ARTICLE; HYDROGENATION; ISOTOPE LABELING; REACTION ANALYSIS; SUZUKI REACTION; SYNTHESIS;

EID: 1842739440     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030329d     Document Type: Article

References (60)

1. Dowhan, W.; Bogdanov, M. New Compr. Biochem. 2002, 36, 1-35.
2. Fielding, C. J.; Fielding, P. E. Biochim. Biophys. Acta 2001, 1553, 175-189.
3. Fielding, P. E.; Russel, J. S.; Spencer, T. A.; Hakamata, H.; Nagao, K.; Fielding, C. J. Biochemistry 2002, 41, 4929-4937.
4. Phosphatidylcholines occur naturally with differing fatty acid chains on C1 and C2, and commercial PCs are mixtures of compounds. Structure 2 shows the C1 palmitoyl, C2 oleoyl version, which is a major component of natural PCs.
5. Chakrabarti, P.; Khorana, H. G. Biochemistry 1975, 14, 5021-5033.
6. Gupta, C. M.; Radhakrishnan, R.; Gerber, G. E.; Olsen, W. L.; Quay, S. C.; Khorana, H. G. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 3139-3143.
7. Schroit, A. J.; Madsen, J.; Ruoha, A. E. Biochemistry 1987, 26, 1812-1819.
8. Perides, G.; Harter, C.; Traub, P. J. Biol. Chem. 1987, 262, 13742-13749.
9. Zachowski, A.; Fellmann, P.; Herve, P.; Devaux, P. F. FEBS Lett. 1987, 223, 315-320.
10. Goldmann, W. H.; Niles, J. L.; Arnaout, M. A. Eur. J. Biochem. 1999, 261, 155-162.
11. Janssen, M. J. F. W.; van Voorst, F.; Ploeger, G. E. J.; Mose, P.; Larsen, M. R.; de Kroon, A. I. P. M.; de Kruijff, B. Biochemistry 2002, 41, 5702-5711.
12. Li, G. Ph.D. Dissertation, City University of New York, New York, 2002; Diss. Abstr. Int. B. 2002, 62, 5734; UMI no. 3037416.
13. Li, G. Ph.D. Dissertation, City University of New York, New York, 2002; Diss. Abstr. Int. B. 2002, 62, 5734; UMI no. 3037416.
14. Brunner, J.; Senn, H.; Richards, F. M. J. Biol. Chem. 1980, 255, 3313-3318.
15. Page, G. P.; Rosenbusch, J. P. Biochem. J. 1986, 235, 651-661.
16. Montecucco, C.; Schiavo, G. Biochem. J. 1986, 237, 309-312.
17. Lala, A. K.; Kumar, E. R. J. Am. Chem. Soc. 1993, 115, 3982-3988.
18. Nakatani, Y.; Yamamoto, M.; Diyizou, Y.; Warnock, W.; Dollé, V.; Hahn, W.; Milon, A.; Ourisson, G. Chem. Eur. J. 1996, 2, 129-138.
19. Dormán, G.; Prestwich, G. D. Biochemistry 1994, 33, 5661-5673.
20. Prestwich, G. D.; Dormán, G.; Elliott, J. T.; Marecak, D. M.; Chaudhardy, A. Photochem. Photobiol. 1997, 65, 222-234.
21. Weber, P. J. A.; Beck-Sickinger, A. G. J. Pept. Res. 1997, 49, 375-383.
22. Dac, L. K.; Guenter, H.; Hans, B. Ger. Offen. 1979, DE 2728893, p. 11.
23. Stoffel, W. Methods Enzymol. 1975, 35, 533-541.
24. Ceruso, M.; Prestwich, G. D. Bioorg. Med. Chem. Lett. 1994, 4, 2179-2184.
25. Lee, H.-K.; Denner-Ancona, P.; Sakakibara, J.; Ono, T.; Prestwich, G. D. Arch. Biochem. Biophys. 2000, 381, 43-52.
26. Markovic, D. Z.; Durand, T.; Patterson, L. K. Photochem. Photobiol. 1990, 51, 389-394.
27. Taber, D. F.; Sethuranam, M. R. J. Org. Chem. 2000, 65, 254-255.
28. Nakatani, K.; Dohno, C.; Nakamura, T.; Saito, I. Tetrahedron Lett. 1998, 39, 2779-2782.
29. Johnson, C. R.; Braun, M. P. J. Am. Chem. Soc. 1993, 115, 11014-11015.
30. Chemler, S. R.; Danishefsky, S. J. Org. Lett. 2000, 2, 2695-2698.
31. Bosch, M. P.; Petschen, I.; Guerrero, A. Synthesis 2000, 300-304.
32. Ali, S.; Bittman, R. Chem. Phys. Lipids 1989, 50, 11-21.
33. Chupin, V. V.; Ostapenko, O. V.; Klykov, V. N.; Anikin, M. V.; Serebrenikova, G. A. Chem. Phys. Lipids 1996, 81, 35-43.
34. Bittman, R. In Phospholipids Handbook; Cevc, G., Ed.; Dekker: New York, 1993; Chapter 6, pp 141-232.
35. Hermetter, A.; Stütz, H.; Franzmair, R.; Paltauf, F. Chem. Phys. Lipids 1989, 50, 57-62.
36. Borsotti, G.; Guglielmetti, G.; Spera, S.; Battistel, E. Tetrahedron 2001, 57, 10219-10227.
37. Guivisdalsky, P. N.; Bittman, R. J. Org. Chem. 1989, 54, 4637-4642.
38. Guivisdalsky, P. N.; Bittman, R. J. Org. Chem. 1989, 54, 4643-4648.
39. Dale, D. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
40. Cimetiere, B.; Jacob, L.; Julia, M. Tetrahedron Lett. 1986, 27, 6329-6332.
41. Russel, J. S. Ph.D. Dissertation, Dartmouth College, Hanover, NH, 1999.
42. Seela, F.; Fröhlich, T. Helv. Chim. Acta 1994, 77, 399-408.
43. 31P NMR or other means is reported.
44. Nakajima, N.; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139-4142.
45. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron 1982, 23, 885-888.
46. Batchelor, J. G.; Cushley, R. J.; Prestegard, J. H. J. Org. Chem. 1974, 39, 1698-1705.
47. Batchelor, J. G.; Prestegard, J. H.; Cushley, R. J.; Lipsky, S. R. J. Am. Chem. Soc. 1973, 95, 6358-6364.
48. 3CN is available from American Radiolabeled Chemicals, St. Louis, MO.
49. Hutchins, R. O.; Kandasamy, D.; Maryanoff, C. A.; Masiliamani, D.; Maryanoff, B. E. J. Org. Chem. 1977, 42, 82-91.
50. Bailey, W. F.; Khanolkav, A. D.; Gavaskar, K. V. J. Am. Chem. Soc. 1992, 114, 8053-8060.
51. Molander, G. A.; Shakya, S. R. J. Org. Chem. 1996, 61, 5885-5894.
52. Hauser, C. F.; Brooks, T. W.; Miles, M. L.; Raymonds, M. A.; Butler, G. B. J. Org. Chem. 1963, 28, 372-379.
53. Dalcanale, E. J. Org. Chem. 1986, 51, 567-569.
54. Zhao, H.; Neamati, N.; Pommier, Y.; Burke, Jr., T. R. Heterocycles 1997, 45, 2277-2282.
55. Posner, G. H. Org. React. 1975, 22, 253-400.
56. (a) Bosshard, H. H.; Mory, R.; Schmid, M.; Zollinger, H. Helv. Chim. Acta 1959, 42, 1653-1658.
57. (b) Egawa, Y.; Okuda, T. Chem. Pharm. Bull. 1963, 11, 589-596.
58. Wessel, H.-P.; Iversen, T.; Bundle, D. R. J. Chem. Soc., Perkin Trans. 1 1985, 2247-2250.
59. Stowell, J. C. J. Org. Chem. 1970, 35, 244-245.
60. Banwell, M. G.; Bui, C. T.; Simpson, G. W. J. Chem. Soc., Perkin Trans. 1 1978, 791-799.