Superoxidation of bisretinoids

Angewandte Chemie - International Edition

Volumn 44, Issue 43, 2005, Pages 7097-7100

  Washington, Ilyas ^a   Jockusch, Steffen ^a   Itagaki, Yasuhiro ^a   Turro, Nicholas J ^a   Nakanishi, Koji ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

Alkenes; Bisretinoids; Carotenoids; Photochemistry; Singlet oxygen

Indexed keywords

OXIDATION; OXYGEN; PHOTOCHEMICAL REACTIONS;

RETINOID POLYENES; SINGLET OXYGEN; SUPEROXIDATION;

ORGANIC POLYMERS;

OXYGEN; RETINOID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

MOLECULAR STRUCTURE; OXIDATION-REDUCTION; OXYGEN; RETINOIDS;

EID: 27744607631     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200501346     Document Type: Article

References (25)

1. For a review on retinoids, see: "Vitamin A (retinoids)": J. L. Napoli in Encyclopedia of Biological Chemistry, Vol. 4 (Eds.: W. J. Lennarz, M. D. Lane), Elsevier, Oxford, 2004, pp. 354-359.
2. For a review on the photochemistry of retinoids, see: P. P. Fu, S. H. Cheng, L. Coop, Q. Xia, S. J. Culp, W. H. Tolleson, W. G. Wamer, P. C. Howard, J. Environ. Sci. Health Part C 2003, 21, 165-196.
3. a) G. Crank; M. S. Pardijanto, J. Photochem. Photobiol. A 1995, 8, 93-100;
4. b) K. Suyama, T. Yeow, S. Nakai, J. Agric. Food Chem. 1983, 31, 22-26;
5. c) M. Mousseron-Canet, Methods Enzymol. 1971, 18, 591-615;
6. d) K. Tsujimoto, H. Hozoji, M. Ohashi, M. Watanabe, H. Hattori, Chem. Lett. 1984, 1673-1676;
7. e) M. H. Baron, M. J. Coulange, C. Coupry, D. Baron, J. Favrot, M. M. Abo-Aly, Photochem. Photobiol. 1989, 49, 736-751;
8. f) K. B. Clark, J. A. Howard, A. J. Oyler, J. Am. Chem. Soc. 1997, 119, 9560-9561;
9. g) A. J. Oyler, M. G. Motto, R. E. Naldi, K. L. Facchine, P. F. Hamburg, D. J. Burinsky, R, Dunphy, M. L. Cotter, Tetrahedron 1989, 45, 7679-7694;
10. h) G. W. Burton, L. Huges, K. U. Ingold, D. A. Lindsy, D. J. Moffatt, Tetrahedron 1993, 49, 911-928.
11. a) S. Ben-Shabat, Y. Itagaki, S. Jockusch, J. R. Sparrow, N. J. Turro, K. Nakanishi, Angew. Chem. 2002, 114, 842-845;
12. Angew. Chem. Int. Ed. 2002, 41, 814-817;
13. b) J. R. Sparrow, H. R. Vollmer-Snarr, J. Zhou, B. Cai, S. Jockusch, Y. Itagaki, K. Nakanishi, J. Biol. Chem. 2003, 278, 18207-18213.
14. J. V. Morris, M. A. Mahaney, J. R. Huber, J. Phys. Chem. 1976, 80, 969-974.
15. a) A. T. C. Tsin, P. A. Fernandez, J. M. Gallas, J. P. Chambers, Life Sci. 1988, 43 1379-1384;
16. b) A. J. Thomson, J. Chem. Phys. 1969, 51, 4106-4116.
17. a) K. Chihara, W. H. Waddell, J. Am. Chem. Soc. 1980, 102, 2963-2968;
18. b) T. Takemura, K. Chihara, R. S. Becker, P. K. Das, G. L. Hug, J. Am. Chem. Soc. 1980, 102, 2604-2609.
19. G. E. Khalil, A. Chang, M. Gouterman, J. B. Callis, L. R. Dalton, N. J. Turro, S. Jockusch, Rev. Sci. Instrum. 2005, 76, 054101/1-054101/8.
20. A. A. Krasnovsky, V. E. Kagan, FEBS Lett. 1979, 108, 152-154.
21. a) R. C. Kanner, C. S. Foote, J. Am. Chem. Soc. 1992, 114, 682-688;
22. b) X. G. Fu, L. P. Zhang, L. Z. Wu, C. H. Tung, J. Photosci. 2003, 10, 175-180.
23. J. Dillon, E. R. Gaillard, P. Bilski, C. F. Chignell, K. J. Reszka, Photochem. Photobiol. 1996, 63, 680-685.
24. E. R. Gaillard, L. B. Avalle, L. M. M. Keller, Z. Wang, K. J. Reszka, J. P. Dillon, Exp. Eye Res. 2004, 79, 313-319.
25. For a review on polyene natural products, see: C. Thirsk, A. Whiting, J. Chem. Soc. Perkin Trans. 1 2002, 999-1023.