The carbon-skeleton rearrangement in tropane alkaloid biosynthesis

Journal of the American Chemical Society

Volumn 130, Issue 32, 2008, Pages 10684-10690

  Sandala, Gregory M ^a,b   Smith, David M ^c   Radom, Leo ^a,b  

^a UNIVERSITY OF SYDNEY   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

^c RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMICAL ENGINEERING; BIOCHEMISTRY;

ALKALOID BIOSYNTHESIS; CARBOCATION; HIGH ENERGIES; QUANTUM CHEMISTRY CALCULATIONS;

QUANTUM CHEMISTRY;

CARBON; ENZYME; HYOSCYAMINE; LITTORINE; RADICAL; TROPANE ALKALOID;

ACIDITY; ARTICLE; BIOSYNTHESIS; CALCULATION; ENERGY; FRAGMENTATION REACTION; GAS; IONIZATION; MODULATION; OXIDATION; PROTON TRANSPORT; QUANTUM CHEMISTRY;

ATROPINE; ATROPINE DERIVATIVES; CARBON; CYTOCHROME P-450 ENZYME SYSTEM; MOLECULAR STRUCTURE; OXIDOREDUCTASES;

EID: 49449092833     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja801869a     Document Type: Article

References (57)

1. See, for example: (a) Lounasmaa, M.; Tamminen, T. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 44, pp 1-114.
2. (b) Robins, R. J.; Walton, N. J. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 44, pp 115-187.
3. Robins, R. J.; Bachmann, P.; Woolley, J. G. J. Chem. Soc., Perkin Trans. 1 1994, 6, 615-619.
4. See, for example: Banerjee, R. Chem. Rev. 2003, 103, 2083-2094.
5. Beatrix, B.; Zelder, O.; Kroll, F. K.; Örlygsson, G.; Golding, B. T.; Buckel, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2398-2401.
6. See, for example: Smith, D. M.; Golding, B. T.; Radom, L. J. Am. Chem. Soc. 1999, 121, 9388-9399.
7. Maiti, N.; Widjaja, L.; Banerjee, R. J. Biol. Chem. 1999, 274, 32733-32737.
8. Ollagnier, S.; Kervio, E.; Rétey, J. FEBS Lett. 1998, 437, 309-312.
9. (a) Wang, S. C.; Frey, P. A. Trends Biochem. Sci. 2007, 32, 209.
10. (b) Wang, S. C.; Frey, P. A. Trends Biochem. Sci. 2007, 32, 101-110.
11. Frey, P. A.; Hegeman, A. D.; Reed, G. H. Chem. Rev. 2006, 106, 3302-3316.
12. (a) Chesters, N. C. J. E.; Walker, K.; O'Hagan, D.; Floss, H. G. J. Am. Chem. Soc. 1996, 118, 925-926.
13. (b) Patterson, S.; O'Hagan, D. Phytochemistry 2002, 61, 323-329.
14. Zabetakis, I.; Edwards, R.; Hamilton, J. T. G.; O'Hagan, D. Plant Cell Rep. 1998, 18, 341-345.
15. Li, R.; Reed, D. W.; Liu, E.; Nowak, J.; Pelcher, L. E.; Page, J. E.; Covello, P. S. Chem. Biol. 2006, 13, 513-520.
16. Wong, C. W.; Hamilton, J. T. G.; O'Hagan, D.; Robins, R. J. Chem. Commun. 1998, 9, 1045-1046.
17. O'Hagan, D.; Robins, R. J. Chem. Soc. Rev. 1998, 27, 207-212.
18. 3. In Section 3.2.3, these models are further truncated with R = H. A single nomenclature for the various reaction intermediates (i.e., 3a, 4a, 3b, 4b) has nevertheless been adopted for the sake of simplicity.
19. V=O notation for the prospective oxidant here, as the ligand environment and its oxidation state are so far unknown. See also, ref 14.
20. Newcomb, M.; Chanrasena, R. E. P. Biochem. Biophys. Res. Commun. 2005, 338, 394-403.
21. See, for example: (a) Ortiz de Montellano, P. R. Cytochrome P450 Structure, Mechanism, and Biochemistry, 2nd ed.; Plenum: New York, 1995.
22. (b) Ortiz de Montellano, P. R. Cytochrome P450 Structure, Mechanism, and Biochemistry, 3rd ed.; Plenum Kluwer: New York, 2005.
23. Jiang, Y.; He, X.; Ortiz de Montellano, P. R. Biochemistry 2006, 45, 533-542.
24. (a) Guengerich, F. P. Chem. Res. Toxicol. 2001, 14, 611-650.
25. (b) Isin, E. M.; Guengerich, F. P. Biochim. Biophys. Acta 2007, 1770, 314-329.
26. (a) Shaik, S.; Filatov, M.; Schroder, D.; Schwarz, H. Chem. Eur. J. 1998, 4, 193-199.
27. (b) de Visser, S. P.; Ogliaro, F.; Sharma, P. K.; Shaik, S. Angew. Chem., Int. Ed. 2002, 41, 1947-1951.
28. (c) de Visser, S. P.; Shaik, S.; Sharma, P. K.; Kumar, D.; Thiel, W. J. Am. Chem. Soc. 2003, 125, 15779-15788.
29. (d) Shaik, S.; Kumar, D.; de Visser, S. P.; Altun, A.; Thiel, W. Chem. Rev. 2005, 105, 2279-2328.
30. (e) Shaik, S.; Hirao, H.; Kumar, D. Acc. Chem. Res. 2007, 40, 532-542.
31. (a) Cavalieri, E. L.; Rogan, E. C. Xenobiotica 1995, 25, 677-688.
32. (b) Sato, H.; Guengerich, F. P. J. Am. Chem. Soc. 2000, 122, 8099-8100.
33. Stearns, R. A.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1985, 107, 4081-4082.
34. (a) Newcomb, M.; Le Tadic-Biadatti, M.-H.; Chestney, D. L.; Roberts, E. S.; Hollenberg, P. F. J. Am. Chem. Soc. 1995, 117, 12085-12091.
35. (b) Newcomb, M.; Shen, R.; Choi, S.-Y.; Toy, P. H.; Hollenberg, P. F.; Vaz, A. D. N.; Coon, M. J. J. Am. Chem. Soc. 2000, 122, 2677-2686.
36. Baciocchi, E.; Lanzalunga, O.; Lapi, A.; Manduchi, L. J. Am. Chem. Soc. 1998, 120, 5783-5787.
37. Ullrich, V.; Brugger, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1911-1919.
38. Smith, D. M.; Golding, B. T.; Radom, L. J. Am. Chem. Soc. 2001, 123, 1664-1675.
39. (a) Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
40. (b) Jensen, F. Introduction to Computational Chemistry, 2nd ed.; Wiley: Chichester, U.K., 2007.
41. Koch, W.; Holthausen, M. C. A Chemist's Guide to Density Functional Theory, 2nd ed.; Wiley: New York, 2001.
42. MOLPRO 2002.6 is a package of ab initio programs written by Werner, H.-J. et al.
43. Frisch, M. J. et al. Gaussian 03, revisions D.01 and E.01; Gaussian, Inc.: Wallingford CT, 2004.
44. Merrick, J. P.; Moran, D.; Radom, L. J. Phys. Chem. A 2007, 111, 11683-11700.
45. Chih, H.-W.; Marsh, E. N. G. J. Am. Chem. Soc. 2000, 122, 10732-10733.
46. (a) Wetmore, S. D.; Smith, D. M.; Golding, B. T.; Radom, L. J. Am. Chem. Soc. 2001, 123, 7963-7972.
47. (b) Sandala, G. M.; Smith, D. M.; Marsh, E. N. G.; Radom, L. J. Am. Chem. Soc. 2007, 129, 1623-1633.
48. (a) Menon, A. S.; Wood, G. P. F.; Moran, D.; Radom, L. J. Phys. Chem. A 2007, 111, 13638-13644, and references therein.
49. (b) Menon, A. S.; Wood, G. P. F.; Moran, D.; Radom, L. J. Phys. Chem. A 2008, 112, 5554.
50. Newcomb, M.; Chestney, D. L. J. Am. Chem. Soc. 1994, 116, 9753-9754.
51. Apeloig, Y.; Schleyer, P. v. R.; Pople, J. A. J. Am. Chem. Soc. 1977, 99, 5901-5909.
52. Kamachi, T.; Toraya, T.; Yoshizawa, K. Chem. Eur. J. 2007, 13, 7864-7873.
53. Shibata, N.; Masuda, J.; Tobimatsu, T.; Toraya, T.; Suto, K.; Morimoto, Y.; Yasuoka, N. Structure 1999, 7, 997-1008.
54. (a) Dyke, J. M.; Jonathan, N.; Lee, E.; Morris, A.; Winter, M. Phys. Scr. 1977, 16, 197-201.
55. (b) Houle, F. A.; Beauchamp, J. L. J. Am. Chem. Soc. 1979, 101, 4067-4074.
56. Ionization Energies of Atoms and Atomic Ions. In CRC Handbook of Chemistry and Physics, Internet Version 2008, 88th ed.; Lide, D. R., Ed.; CRC Press/Taylor and Francis: Boca Raton, FL, 2008.
57. Akhtar, M.; Wright, J. N.; Shyadehi, A. Z.; Robichaud, P. Pure Appl. Chem. 1994, 66, 2387-2390.