Effect of isotopically sensitive branching on product distribution for pentalenene synthase: Support for a mechanism predicted by quantum chemistry

Journal of the American Chemical Society

Volumn 134, Issue 28, 2012, Pages 11369-11371

  Zu, Liansuo ^a   Xu, Meimei ^b   Lodewyk, Michael W ^a   Cane, David E ^c   Peters, Reuben J ^b   Tantillo, Dean J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b IOWA STATE UNIVERSITY   (United States)

^c BROWN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCATIONS; CASCADE REACTIONS; PRODUCT DISTRIBUTIONS; QUANTUM-CHEMICAL CALCULATION; SESQUITERPENES; SYNTHASES;

CHEMISTRY; SYNTHESIS (CHEMICAL);

QUANTUM CHEMISTRY;

ENZYME; PENTALENENE SYNTHASE; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; ENZYME LOCALIZATION; QUANTUM CHEMISTRY;

CATIONS; INTRAMOLECULAR LYASES; MUTATION; QUANTUM THEORY;

EID: 84863931099     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3043245     Document Type: Article

References (47)

1. Seto, H.; Yonehara, H. J. Antibiot. 1980, 33, 92-93
2. Cane, D. E.; Sohng, J. K.; Williard, P. G. J. Org. Chem. 1992, 57, 844-852
3. Cane, D. E. Compr. Nat. Prod. Chem. 1999, 2, 155-200
4. Cane, D. E. Chem. Rev. 1990, 90, 1089-1103
5. Davis, E. M.; Croteau, R. Top. Curr. Chem. 2000, 209, 53-95
6. Tantillo, D. J. Nat. Prod. Rep. 2011, 28, 1035-1053
7. Cane, D. E.; Tillman, A. M. J. Am. Chem. Soc. 1983, 105, 122-124
8. Cane, D. E.; Sohng, J.-K.; Lamberson, C. R.; Rudnicki, S. M.; Wu, Z.; Lloyd, M. D.; Oliver, J. S.; Hubbard, B. R. Biochemistry 1994, 33, 5846-5857
9. For a recent review on sesquiterpene synthases, see: Miller, D. J.; Allemann, R. K. Nat. Prod. Rep. 2012, 29, 60-71
10. Cane, D. E.; Abell, C.; Lattman, R.; Kane, C. T.; Hubbard, B. R.; Harrison, P. H. M. J. Am. Chem. Soc. 1988, 110, 4081-4082
11. Cane, D. E.; Oliver, J. S.; Harrison, P. H. M.; Abell, C.; Hubbard, B. R.; Kane, C. T.; Lattman, R. J. Am. Chem. Soc. 1990, 112, 4513-4524
12. Harrison, P. H. M.; Oliver, J. S.; Cane, D. E. J. Am. Chem. Soc. 1988, 110, 5922-5923
13. Seemann, M.; Zhai, G.; Umezawa, K.; Cane, D. E. J. Am. Chem. Soc. 1999, 121, 591-592
14. Seemann, M.; Zhai, G.; de Kraker, J.-W.; Paschall, C. M.; Christianson, D. W.; Cane, D. E. J. Am. Chem. Soc. 2002, 124, 7681-7689
15. Lesburg, C. A.; Zhai, G.; Cane, D. E.; Christianson, D. W. Science 1997, 277, 1820-1824
16. Gutta, P.; Tantillo, D. J. J. Am. Chem. Soc. 2006, 128, 6172-6179
17. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1972, 11, 129-130
18. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1972, 11, 130-131
19. Reetz, M. T. Tetrahedron 1973, 29, 2189-2194
20. Reetz, M. T. Adv. Organomet. Chem. 1977, 16, 33-65
21. Hoffmann, R.; Williams, J. E., Jr. Helv. Chim. Acta 1972, 55, 67-75
22. Fernández, I.; Cossío, F. P.; Sierra, M. A. Chem. Rev. 2009, 109, 6687-6711
23. Ohfune, Y.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1976, 17, 2869-2872
24. Misumi, S.; Ohtsuka, T.; Ohfune, Y.; Sugita, K.; Shirahama, H.; Matsumoto, T. Tetrahedron Lett. 1979, 20, 31-34
25. Pattenden, G.; Teague, S. J. Tetrahedron 1987, 43, 5637-5652
26. Jones, J. P.; Korzekwa, K. R.; Rettie, A. E.; Trager, W. F. J. Am. Chem. Soc. 1986, 108, 7074-7078
27. Croteau, R. B.; Wheeler, C. J.; Cane, D. E.; Ebert, R.; Ha, H.-J. Biochemistry 1987, 26, 5383-5389
28. Wagschal, K. C.; Pyun, H.-J.; Coates, R. M.; Croteau, R. Arch. Biochem. Biophys. 1994, 308, 477-487
29. Nes, W. D.; McCourt, B. S.; Marshall, J. A.; Ma, J.; Dennis, A. L.; Lopez, M.; Li, H.; He, L. J. Org. Chem. 1999, 64, 1535-1542
30. Schenk, D. J.; Starks, C. M.; Manna, K. R.; Chappell, J.; Noel, J. P.; Coates, R. M. Arch. Biochem. Biophys. 2006, 448, 31-44
31. He, X.; Cane, D. E. J. Am. Chem. Soc. 2004, 126, 2678-2679
32. Wagschal, K.; Savage, T. J.; Croteau, R. Tetrahedron 1991, 47, 5933-5944
33. Pyun, H. J.; Coates, R. M.; Wagschal, K. C.; McGeady, P.; Croteau, R. B. J. Org. Chem. 1993, 58, 3998-4009
34. http://www.massfinder.com.
35. Cane, D. E.; Tandon, M. Tetrahedron Lett. 1994, 35, 5355-5358
36. Bigeleisen, J.; Mayer, M. G. J. Chem. Phys. 1947, 15, 261-267
37. D reported in the text reflects deprotonation from different conformers of C. See the Supporting Information for additional details
38. Hong, Y. J.; Tantillo, D. J. Chem. Commun. 2012, 48, 1571-1573
39. Roy, A.; Roberts, F. G.; Wilderman, P. R.; Zhou, K.; Peters, R. J.; Coates, R. M. J. Am. Chem. Soc. 2007, 129, 12453-12460
40. Greenhagen, B. T.; O'Maille, P. E.; Noel, J. P.; Chappell, J. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 9826-9831
41. Shishova, E. Y.; Di Costanzo, L.; Cane, D. E.; Christianson, D. W. Biochemistry 2007, 46, 1941-1951
42. Peters, R. J.; Croteau, R. B. Arch. Biochem. Biophys. 2003, 417, 203-211
43. Hong, Y. J.; Tantillo, D. J. Org. Biomol. Chem. 2010, 8, 4589-4600
44. Garms, S.; Chen, F.; Boland, W.; Gershenzon, J.; Köllner, T. G. Phytochemistry 2012, 75, 6-13
45. Zhou, K.; Peters, R. J. Chem. Commun. 2011, 47, 4074-4080
46. Mehta, G.; Umarye, J. D. Tetrahedron Lett. 2001, 42, 8101-8104
47. Fricke, C.; Hardt, I. H.; König, W. A.; Joulain, D.; Zygadlo, J. A.; Guzman, C. A. J. Nat. Prod. 1999, 62, 694-696