Oxidatively truncated docosahexaenoate phospholipids: Total synthesis, generation, and peptide adduction chemistry

Journal of Organic Chemistry

Volumn 68, Issue 10, 2003, Pages 3749-3761

  Gu, Xiaorong ^a   Sun, Mingjiang ^a   Gugiu, Bogdan ^a   Hazen, Stanley ^b   Crabb, John W ^b   Salomon, Robert G ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

^b LERNER RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMMUNOLOGY; MIXTURES; OXIDATION; PROTEINS; SYNTHESIS (CHEMICAL);

MACULAR DEGENERATION;

PHOSPHOLIPIDS;

1 PALMITOYL 2 SUCCINOYLGLYCERO 3 PHOSPHATIDYLCHOLINE; 2 (4 HYDROXY 7 OXOHEPT 5 ENOYL) 1 PALMITOYLGLYCERO 3 PHOSPHATIDYLCHOLINE; 2 (6 CARBOXY 4 OXOHEX 5 ENOYL) 1 PALMITOYLGLYCERO 3 PHOSPHATIDYLCHOLINE; COPPER ION; DOCOSAHEXAENOIC ACID; LYSOPHOSPHATIDYLCHOLINE; MYELOPEROXIDASE; PHOSPHOLIPID; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; IMMUNODETECTION; OXIDATION; PHOSPHOLIPID SYNTHESIS; PHOTORECEPTOR; PROTEIN MODIFICATION; RETINA; RETINA DISEASE; RETINA MACULA AGE RELATED DEGENERATION;

EID: 0038627633     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026721t     Document Type: Article

References (37)

1. Fliesler, S. J.; Anderson, R. E. Prog. Lipid Res. 1983, 22, 79-131.
2. Kuwabara, T. Am. J. Ophthalmol. 1970, 70, 187-98.
3. Young, R. W. J. Cell Biol. 1967, 33, 61-72.
4. Young, R. W. Ann. Ophthalmol. 1973, 5, 843-54.
5. Bynoe, L. A.; Del Priore, L. V.; Hornbeck, R. Graefes Arch. Clin. Exp. Ophthalmol. 1998, 236, 230-3.
6. Rozanowska, M.; Jarvis-Evans, J.; Korytowski, W.; Boulton, M. E.; Burke, J. M.; Sarna, T. J. Biol. Chem. 1995, 270, 18825-30.
7. Dontsov, A. E.; Glickman, R. D.; Ostrovsky, M. A. Free Radic. Biol. Med. 1999, 26, 1436-46.
8. Hill, H. Z.; Li, W.; Xin, P.; Mitchell, D. L. Pigment Cell Res. 1997, 10, 158-61.
9. Sayre, L. M.; Sha, W.; Xu, G.; Kaur, K.; Nadkarni, D.; Subbanagounder, G.; Salomon, R. G. Chem. Res. Toxicol. 1996, 9, 1194-201.
10. Kaur, K.; Salomon, R. G.; O'Neil, J.; Hoff, H. F. Chem. Res. Toxicol. 1997, 10, 1387-96.
11. Watson, A. D.; Leitinger, N.; Navab, M.; Faull, K. F.; Horkko, S.; Witztum, J. L.; Palinski, W.; Schwenke, D.; Salomon, R. G.; Sha, W.; Subbanagounder, G.; Fogelman, A. M.; Berliner, J. A. J. Biol. Chem. 1997, 272, 13597-607.
12. Podrez, E. A.; Poliakov, E.; Shen, Z.; Zhang, R.; Deng, Y.; Sun, M.; Finton, P. J.; Shan, L.; Febbraio, M.; Hajjar, D. P.; Silverstein, R. L.; Hoff, H. F.; Salomon, R. G.; Hazen, S. L. J. Biol. Chem. 2002, 277, 38517-23.
13. Podrez, E. A.; Poliakov, E.; Shen, Z.; Zhang, R.; Deng, Y.; Sun, M.; Finton, P. J.; Shan, L.; Gugiu, B.; Fox, P. L.; Hoff, H. F.; Salomon, R. G.; Hazen, S. L. J. Biol. Chem. 2002, 277, 38503-16.
14. Subbanagounder, G.; Deng, Y.; Borromeoa, C.; Dooley, A. N.; Berliner, J. A.; Salomon, R. G. Vasc. Pharmacol. 2002, 38, 201-209.
15. Deng, Y.; Salomon, R. G. J. Org. Chem. 1998, 63, 7789-7794.
16. Bligh, E.; Dyer, W. Can. J. Biochem. Physiol. 1959, 37, 911-917.
17. Ryeom, S. W.; Sparrow, J. R.; Silverstein, R. L. J. Cell Sci. 1996, 109 (2), 387-95.
18. DeLong, C. J.; Baker, P. R.; Samuel, M.; Cui, Z.; Thomas, M. J. J. Lipid Res. 2001, 42, 1959-68.
19. Deng, Y.; Salomon, R. G. Book of Abstracts. 218th ACS National Meeting, New Orleans, Aug 22-26, 1999; American Chemical Society: Washington, DC, 1999; ORGN-059.
20. Deng, Y.; Salomon, R. G. J. Org. Chem. 2000, 65, 6660-6665.
21. Miller, D. B.; Raychaudhuri, S. R.; Avasthi, K.; Lal, K.; Levison, B.; Salomon, R. G. J. Org. Chem. 1990, 55, 3164-75.
22. Roy, S. C.; Nagarajan, L.; Salomon, R. G. J. Org. Chem. 1999, 64, 1218-1224.
23. Salomon, R. G.; Miller, D. B. Adv. Prostaglan. Thrombox. Leukot. Res. 1985, 15, 323-6.
24. Sha, W.; Salomon, R. G. J. Org. Chem. 2000, 65, 5315-26.
25. Subbanagounder, G.; Salomon, R. G.; Murthi, K. K.; Brame, C.; Roberts, L. J., II. J. Org. Chem. 1997, 62, 7658-7666.
26. Sun, M.; Deng, Y.; Batyreva, E.; Sha, W.; Salomon, R. G. J. Org. Chem. 2002, 67, 3575-3584.
27. Crabb, J. W.; Miyagi, M.; Gu, X.; Shadrach, K.; West, K. A.; Sakaguchi, H.; Kamei, M.; Hasan, A.; Yan, L.; Rayborn, M. E.; Salomon, R. G.; Hollyfield, J. G. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 14682-14687.
28. Lawrence, D. M. Lancet 2002, 360, 1307.
29. Bok, D. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 14619-14621.
30. Dittmer, J. C.; Lester, R. L. J. Lipid Res. 1964, 5, 126-127.
31. Sodeoka, M.; Yamada, H.; Shibasaki, M. J. Am. Chem. Soc. 1990, 112, 4906-4911.
32. Katsuki, T.; Lee, A. W. M.; Ma, P.; Martin, V. S.; Masamune, S. M.; Sharpless, K. B.; Tuddenham, D.; Walker, F. J. J. Org. Chem. 1982, 47, 1373-1378.
33. Trippett, S.; Walker, D. M. J. Chem. Soc. 1961, 1266-1272.
34. Schmid, C. R.; Bryant, J. D.; Dowlatzedah, M.; Phillips, J. L.; Prather, D. E.; Schantz, R. D.; Sear, N. L.; Vianco, C. S. J. Org. Chem. 1991, 56, 4056-4058.
35. Miyashita, M.; Yoshikoshi, A.; Grieco, P. J. Org. Chem. 1977, 42, 3772-3774.
36. Kobayashi, Y.; Shimazaki, T.; Taguchi, H.; Sato, F. J. Org. Chem. 1990, 55, 5324-5335.
37. Schmitt, D.; Shen, Z.; Zhang, R.; Colles, S. M.; Wu, W.; Salomon, R. G.; Chen, Y.; Chisolm, G. M.; Hazen, S. L. Biochem. 1999, 38, 16904-15.