Feasibility of intramolecular proton transfers in terpene biosynthesis - Guiding principles

Journal of the American Chemical Society

Volumn 137, Issue 12, 2015, Pages 4134-4140

  Hong, Young J ^a   Tantillo, Dean J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; BIOSYNTHESIS; QUANTUM CHEMISTRY; TERPENES;

GUIDING PRINCIPLES; INTRAMOLECULAR PROTON TRANSFER; INTRAMOLECULAR PROTON TRANSFER REACTIONS; QUANTUM CHEMICAL CALCULATIONS; TERPENE BIOSYNTHESIS;

PROTON TRANSFER;

ABIETADIENE; ARISTOLOCHENE; CARYOLENE; FUSICOCCADIENE; GERMANICOL; ITALICENE; MACROCARPENE; MILTIRADIENE; PANASINSENE; SESQUITERPENE DERIVATIVE; TAXADIENE; TENUIFOLENE; TERPENE; TRICHODIENE; UNCLASSIFIED DRUG; PROTON;

ARTICLE; BIOSYNTHESIS; CALCULATION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; PROTON TRANSPORT; QUANTUM CHEMISTRY; CHEMISTRY; METABOLISM; QUANTUM THEORY; THERMODYNAMICS;

BIOSYNTHETIC PATHWAYS; MODELS, MOLECULAR; PROTONS; QUANTUM THEORY; TERPENES; THERMODYNAMICS;

EID: 84926288925     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja512685x     Document Type: Article

References (56)

1. Christianson, D. W. Curr. Opin. Chem. Biol. 2008, 12, 141-150
2. Christianson, D. W. Chem. Rev. 2006, 106, 3412-3442
3. Davis, E. M.; Croteau, R. Top. Curr. Chem. 2000, 209, 53-95
4. Cane, D. E. Compr. Nat. Prod. Chem 1999, 2, 155-200
5. Cane, D. E. Chem. Rev. 1990, 90, 1089-1103
6. Frisch, M. J. Gaussian 03, revision D.01; Gaussian, Inc.: Pittsburgh, PA, 2003.
7. Frisch, M. J. Gaussian 09, revision B.01; Gaussian, Inc.: Pittsburgh, PA, 2010, (full references in Supporting Information).
8. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
9. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377
10. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
11. Stephens, P. J.; Devlin, F. J.
12. Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
13. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527
14. Fukui, K. Acc. Chem. Res. 1981, 14, 363-368
15. Matsuda, S. P. T.; Wilson, W. K.; Xiong, Q. Org. Biomol. Chem. 2006, 4, 530-543
16. Zhao, Y.; Truhlar, D. G. J. Phys. Chem. A 2004, 108, 6908-6918
17. Zheng, J.; Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2007, 3, 569-582
18. Tantillo, D. J. Nat. Prod. Rep. 2011, 28, 1035-1053
19. Müller, N.; Falk, A.; Gsaller, G. Ball & Stick V.4.0a12, molecular graphics application for MacOS computers; Johannes Kepler University: Linz, Austria, 2004.
20. Hong, Y. J.; Tantillo, D. J. Org. Lett. 2006, 8, 4601-4604
21. Vedula, L. S.; Cane, D. E.; Christianson, D. W. Biochemistry 2005, 44, 12719-12727
22. Rynkiewicz, M. J.; Cane, D. E.; Christianson, D. W. Biochemistry 2002, 41, 1732-1741
23. Rynkiewicz, M. J.; Cane, D. E.; Christianson, D. W. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 13543-13548
24. Cane, D. E. Pure. Appl. Chem. 1989, 61, 493-496
25. Hong, Y. J.; Tantillo, D. J. Org. Biomol. Chem. 2009, 7, 4101-4109
26. See also: Hong, Y. J.; Tantillo, D. J. J. Am. Chem. Soc. 2014, 136, 2450-2463
27. Kollner, T. G.; Schnee, C.; Li, S.; Svatos, A.; Schneider, B.; Gershenzon, J.; Degenhardt, J. J. Biol. Chem. 2008, 283, 20779-10788
28. Kreipl, A. T.; König, W. A. Phytochemicals 2004, 65, 2045-2049
29. Gutta, P.; Tantillo, D. J. Angew. Chem., Int. Ed. 2005, 44, 2719-2723
30. Ponec, R.; Bultinck, P.; Gutta, P.; Tantillo, D. J. J. Phys. Chem. A 2006, 110, 3785-3789
31. Tantillo, D. J. Chem. Soc. Rev. 2010, 39, 2847-2854
32. Leimner, J.; Marschall, H.; Meier, N.; Weyerstahl, P. Chem. Lett. 1984, 1769-1772
33. Noguchi, H.; Rawlings, B. J. J. Am. Chem. Soc. 1989, 111, 8914-8916
34. Allemann, R. K.; Young, N. J.; Ma, S.; Truhlar, D. G.; Gao, J. J. Am. Chem. Soc. 2007, 129, 13008-13013
35. Deligeorgopoulou, A.; Taylor, S. E.; Forcat, S.; Allemann, R. K. Chem. Commun. 2003, 2162-2163
36. Cane, D. E.; Prabhakaran, P. C.; Oliver, J. S.; McIlwaine, D. B. J. Am. Chem. Soc. 1990, 112, 3209-3210
37. Miller, D. J.; Gao, J.; Truhlar, D. G.; Young, N. J.; Gonzalez, V.; Allemann, R. K. Org. Biomol. Chem. 2008, 6, 2346-2354
38. Yoshihara, K.; Hirose, Y. Bull. Chem. Soc. Jpn. 1975, 48, 2078-2080
39. Tantillo, D. J. J. Phys. Org. Chem. 2008, 21, 561-570
40. Williams, A. Concerted Organic and Bio-Organic Mechanisms; CRC Press: Boca Raton, 2000.
41. Hess, J. B. A. J. Am. Chem. Soc. 2002, 124, 10286-10287
42. Nguyen, Q. N. N.; Tantillo, D. J. Beilstein J. Org. Chem. 2013, 9, 323-331
43. Gutta, P.; Tantillo, D. J. Org. Lett. 2007, 9, 1069-1071
44. Hong, Y. J.; Tantillo, D. J. J. Am. Chem. Soc. 2011, 133, 18249-18256
45. Lin, X.; Hezari, M.; Koepp, A. E.; Floss, H. G.; Croteau, R. Biochemistry 1996, 35, 2968-2977
46. Williams, C. D.; Carroll, B. J.; Jin, Q.; Rithner, C. D.; Lenger, S. R.; Floss, G. H.; Coates, R. M.; Williams, R. M.; Croteau, R. Chem. Biol. 2000, 7, 969-977
47. Chow, S. Y.; Williams, H. J.; Huang, Q.; Nanda, S.; Scott, A. I. J. Org. Chem. 2005, 70, 9997-10003
48. Toyomasu, T.; Tsukahara, M.; Kenmoku, H.; Anada, M.; Nitta, H.; Ohkanda, J.; Mitsuhashi, W.; Sassa, T.; Kato, N. Org. Lett. 2009, 11, 3044-3047
49. Hong, Y. J.; Tantillo, D. J. Nat. Chem. 2009, 1, 384-389
50. Siebert, M. R.; Zhang, J.; Addepalli, S. V.; Tantillo, D. J.; Hase, W. L. J. Am. Chem. Soc. 2011, 133, 8335-8343
51. Siebert, M. R.; Paranjothy, M.; Sun, R.; Tantillo, D. J.; Hase, W. L. J. Chem. Theory Comput. 2012, 8, 1212-1222
52. For leading references, see: Ravn, M. M.; Peters, R. J.; Coates, R. M.; Croteau, R. J. Am. Chem. Soc. 2002, 124, 6998-7006
53. For leading references, see: Zhou, Y. J.; Gao, W.; Rong, Q.; Jin, G.; Chu, H.; Liu, W.; Yang, W.; Zhu, Z.; Li, G.; Zhu, G.; Huang, L.; Zhao, Z. K. J. Am. Chem. Soc. 2012, 134, 3234-3241
54. Hong, Y. J.; Tantillo, D. J. Nat. Chem. 2014, 6, 104-111
55. Surendra, K.; Corey, E. J. J. Am. Chem. Soc. 2008, 130, 8865-8869
56. Note that transition-state structures examined herein generally involve geometries that are allowed by or fall outside of those covered by Baldwin's rules. A recent review: Alabugin, I. V.; Gilmore, K. Chem. Commun. 2013, 49, 11246-11250