Mechanism and stereoselectivity of biologically important oxygenation reactions of the 7-dehydrocholesterol radical

Journal of Organic Chemistry

Volumn 78, Issue 14, 2013, Pages 7023-7029

  Rajeev, Ramanan ^a   Sunoj, Raghavan B ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC HYDROGEN; C-O BOND FORMATION; MECHANISTIC PATHWAYS; PRODUCT DISTRIBUTIONS; RADICAL OXYGENATION; RELATIVE ENERGIES; STEREOCONTROLLING; STERIC INTERACTIONS;

FREE RADICALS; FUNCTIONAL GROUPS;

CHEMICAL BONDS;

7 DEHYDROCHOLESTEROL; CARBON; CHOLESTEROL; HYDROGEN; METHYL GROUP; OXYGEN; RADICAL;

ARTICLE; CHEMICAL ANALYSIS; COVALENT BOND; DENSITY; DENSITY FUNCTIONAL THEORY; DISTORTION INTERACTION ANALYSIS; ENERGY; FRAGMENTATION REACTION; OXYGENATION; QUANTITATIVE ANALYSIS; STEREOCHEMISTRY;

DEHYDROCHOLESTEROLS; FREE RADICALS; MOLECULAR CONFORMATION; OXYGEN; QUANTUM THEORY; STEREOISOMERISM;

EID: 84880516242     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo4008496     Document Type: Article

References (32)

1. Jahn, U.; Galano, J. M.; Durand, T. Angew. Chem., Int. Ed. 2008, 47, 5894
2. Esterbauer, H.; Gebicki, J.; Puhl, H.; Jurgens, G. Free Radical Biol. Med. 1992, 13, 341
3. Korade, Z.; Xu, L.; Shelton, R.; Porter, N. A. J. Lipid Res. 2010, 51, 3259
4. Janowski, B. A.; Willy, P. J.; Devi, T. R.; Falck, J. R.; Mangelsdorf, D. J. Nature 1996, 383, 728
5. Raoult, D.; Audic, S.; Robert, C.; Abergel, C.; Renesto, P.; Ogata, H.; Scola, B. L.; Suzan, M.; Claverie, J. M. Science 2004, 306, 1344
6. Lang, M.; Murat, S.; Clark, A. G.; Gouppil, G.; Blais, C.; Matzkin, L. M.; Guittard, E.; Yanagawa, T. Y.; Kataoka, H.; Niwa, R.; Lafont, R.; Villemant, C. D.; Orgogozo, V. Science 2012, 337, 1658
7. Shen, Y.; Wollam, J.; Magner, D.; Karalay, O.; Antebi, A. Science 2012, 338, 1472
8. Yin, H.; Xu, L.; Porter, N. A. Chem. Rev. 2011, 111, 5944
9. Korade, Z.; Xu, L.; Mirnics, K.; Porter, N. A. J. Inherit. Metab. Dis. 2013, 36, 113
10. Iuliano, L. Chem. Phys. Lipids 2011, 164, 457
11. Porter, N. A. Methods Enzymol. 1984, 105, 273
12. Porter, N. A. Acc. Chem. Res. 1986, 19, 262
13. Porter, N. A.; Caldwell, S. E.; Mills, K. A. Lipids 1995, 30, 277
14. Tallman, K. A.; Pratt, D. A.; Porter, N. A. J. Am. Chem. Soc. 2001, 123, 11827
15. Xu, L.; Korade, Z.; Porter, N. A. J. Am. Chem. Soc. 2010, 132, 2222
16. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Clarendon Press: Oxford, 1990.
17. AIM2000 (Version 2.0), The Buro fur Innovative Software, SBK-Software, Bielefeld, Germany.
18. Frisch, M. J., Gaussian 09 Revision A.02; Gaussian, Inc., Wallingford, CT, 2004. The complete list of citations is provided in Supporting Information
19. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154
20. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523
21. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 1
22. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
23. Diefenbach, A.; Bickelhaupt, F. M. J. Phys. Chem. A 2004, 108, 8460
24. Jong, G. T. D.; Visser, R.; Bickelhaupt, F. M. J. Organomet. Chem. 2006, 691, 4341
25. Jong, G. T. D.; Bickelhaupt, F. M. Chem. Phys. Chem. 2007, 8, 1170
26. Jong, G. T. D.; Bickelhaupt, F. M. J. Chem. Theory Comput. 2007, 3, 514
27. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 10646
28. Ess, D. H.; Houk, K. N. J. Am. Chem. Soc. 2008, 130, 10187
29. Hayden, A. E.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 4084
30. Shinisha, C. B.; Sunoj, R. B. J. Am. Chem. Soc. 2010, 132, 12319
31. Rajeev, R.; Sunoj, R. B. Org. Biomol. Chem. 2011, 9, 2123
32. Rajeev, R.; Sunoj, R. B. J. Org. Chem. 2012, 77, 2474