Photochemistry of A1E, a Retinoid with a Conjugated Pyridinium Moiety: Competition between Pericyclic Photooxygenation and Pericyclization

Journal of the American Chemical Society

Volumn 126, Issue 14, 2004, Pages 4646-4652

  Jockusch, Steffen ^a   Ren, Rex X ^a,b   Jang, Young Pyo ^a   Itagaki, Yasuhiro ^a   Vollmer Snarr, Heidi R ^a,c   Sparrow, Janet R ^a   Nakanishi, Koji ^a   Turro, Nicholas J ^a  

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

^b WESLEYAN UNIVERSITY   (United States)

^c Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEUTERIUM; IRRADIATION; METHANOL; ORGANIC SOLVENTS; OXIDATION; STEREOCHEMISTRY;

PERICYCLIZATION; PHOTOCHEMICAL TRANSFORMATION;

PHOTOCHEMICAL REACTIONS;

CARBON TETRACHLORIDE; CHLOROFORM; ENDOPEROXIDE; METHANOL; OXYGEN; OZONE; PEROXIDE; PYRIDINIUM DERIVATIVE; RETINOID; SINGLET OXYGEN; SOLVENT; TERPENOID;

ARTICLE; CHEMICAL REACTION; CHEMOLUMINESCENCE; CYCLIZATION; DIASTEREOISOMER; IRRADIATION; LIGHT; OXIDATION; OXYGENATION; PHOSPHORESCENCE; PHOTOCHEMISTRY; QUANTUM MECHANICS; STEREOCHEMISTRY;

CYCLIZATION; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXIDATION-REDUCTION; PHOTOCHEMISTRY; PHOTOLYSIS; PYRIDINIUM COMPOUNDS; RETINOIDS; SPECTRUM ANALYSIS;

EID: 1842738509     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039048d     Document Type: Article

References (36)

1. Sakai, N.; Decatur, J.; Nakanishi, K.; Eldred, G. E. J. Am. Chem. Soc. 1996, 118, 1559-1560.
2. Ren, R. X.-F.; Sakai, N.; Nakanishi, K., J. Am. Chem. Soc. 1997, 119, 3619-3620.
3. Eldred, G. E.; Lasky, M. R. Nature 1993, 361, 724-726.
4. Parish, C. A.; Hashimoto, M.; Nakanishi, K.; Dillon, J.; Sparrow, J. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 14609-14613.
5. (a) Haralampus-Grynaviski, N. M.; Lamb, L. E.; Clancy, C. M. R.; Skumatz, C.; Burke, J. M.; Sarna, T.; Simon, J. D. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 3179-3184.
6. (b) Lamb, L. E.; Simon, J. D. Photochem. Photobiol. 2004, 79, 127-136.
7. Mata, N. L.; Weng, J.; Travis, G. H. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 7154-7159.
8. Shaban, H.; Richter, C. Biol. Chem. 2002, 383, 537-545.
9. Sparrow, J. R.; Zhou, J.; Ben-Shabat, S.; Vollmer, H.; Itagaki, Y.; Nakanishi, K. Invest. Ophthalmol. Visual Sci. 2002, 43, 1222-1227.
10. Roberts, J. E.; Kukielczak, B. M.; Hu, D.-N.; Miller, D. S.; Bilski, P.; Sik, R. H.; Motten, A. G.; Chigneli, C. F. Photochem. Photobiol. 2002, 75, 184-190.
11. Ben-Shabat, S.; Itagaki, Y.; Jockusch, S.; Sparrow, J.; Turro, N. J.; Nakanishi, K. Angew. Chem., Int. Ed. 2002, 41, 814-817.
12. Sparrow, J.; Vollmer-Snarr, H. R.; Zhou, J.; Jang, Y. P.; Jockusch, S.; Itagaki, Y.; Nakanishi, K. J. Biol. Chem. 2003, 278, 18207-18213.
13. Kaiser, E. M.; Bartling, G. J.; Thomas, W. R.; Nichols, S. B.; Nash, D. R. J. Org. Chem. 1973, 38, 71.
14. Levine, R.; Dimmig, D. A.; Kadunce, W. M. J. Org. Chem. 1974, 39, 3834.
15. Pawlak, A.; Wrona, M.; Rozanowska, M.; Zareba, M.; Lamb, L. E.; Roberts, J. E.; Simon, J. D.; Sarna, T. Photochem. Photobiol. 2003, 77, 253-258.
16. Hochstrasser, R. M.; Narva, D. L.; Nelson, A. C. Chem. Phys. Lett. 1976, 43, 15-19.
17. Doukas, A. G.; Junnarkar, M. R.; Chandra, D.; Alfano, R. R.; Callender, R. H. Chem. Phys. Lett. 1983, 100, 420-424.
18. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry, 2nd ed.: Mercel Dekker: New York, 1993.
19. Wintgens, V.; Johnston, L. J.; Scaiano, J. C. J. Am. Chem. Soc. 1988, 110, 511.
20. Rodgers, M. A. J. J. Am. Chem. Soc. 1983, 105, 6201-6205.
21. Ogilby, P. R.; Foote, C. S. J. Am. Chem. Soc. 1983, 105, 3423-3430.
22. Hurst, J. R.; Schuster, G. B. J. Am. Chem. Soc. 1983, 105, 5756-5760.
23. Schmidt, R.; Afshari, E. Ber. Bunsen-Ges. Phys. Chem. 1992, 96, 788-794.
24. Wasserman, H. H.; Larsen, D. L. J. Chem. Soc., Chem. Commum. 1972, 5, 253-254.
25. Adam, W.; Prein, M. Acc. Chem. Res. 1996, 29, 275-283.
26. Toumaire, C.; Croux, S.; -T., M. M.; Beck, I.; Hocquaux, M.; Braun, A. M.; Oliveros, E. J. Photochem. Photobiol., B 1993, 205-215.
27. Khan, A. U.; Kasha, M. Proc. Natl. Acad. Sci, U.S.A. 1979, 76, 6047-6049.
28. Rodgers, M. A. J.; Bates, A. L. Photochem. Photobiol. 1980, 31, 533-537.
29. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Kluwer Academic/Plenum Publishers: New York, 1999.
30. Monroe, B. M. J. Am. Chem. Soc. 1981, 103, 7253.
31. Montenegro, M. A.; Nazareno, M. A.; Durantini, E. N.; Borsarelli, C. D. Photochem. Photobiol. 2002, 75, 353-361.
32. Turro, N. J. Modern Molecular Photochemistry; University Science Books: Sausalito, CA, 1991.
33. Liu, R. S. H.; Asato, A. E. Tetrahedron 1969, 40, 1931-1969.
34. Trehan, A.; Liu, R. S. H. Tetrahedron Lett. 1988, 29, 419-422.
35. Woodward, R. B.; Hoffman, R. The Conservation of Orbital Symmetry; Academic Press: New York, 1970.
36. Harper, W. S.; Gaillard. E. R. Photochem. Photobiol. 2001, 73, 71-76.