Computational Simulation of the Terminal Biogenesis of Sesquiterpenes: The Case of 8-Epiconfertin

Quantum Biochemistry

Volumn , Issue , 2010, Pages 623-642

  Barquera Lozada, José Enrique ^a   Cuevas, Gabriel ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

8 epiconfertin; Biogenesis; Computational simulation; Reaction mechanism; Sesquiterpenes

Indexed keywords

EID: 79953836973     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527629213.ch22     Document Type: Chapter

References (97)

1. Herrera, A.L. (1942) Science, 96, 14.
2. Negrón-Mendoza, A. (1994) J. Biol. Phys., 20, 11-15.
3. Lehninger, A.L. (1970) Biochemistry, Worth Publisher, New York, p. 483.
4. Manitto, P. (1981) Biosynthesis of Natural Products, John Wiley & Sons, Inc., New York, p. 10.
5. Clement, J.S., Mabry, T.J., Wyler, H., and Dreiding, A.S. (1994) Chemical review and evolutionary significance of the betalains, in Caryophyllales (eds H.D. Behnke and T.J. Mabry), Springler, Berlin, pp. 247-261.
6. Croteau, R., Kutchan, T.M., and Lewis, G.N. (2000) Natural products (secondary metabolites), in Biochemistry and Molecular Biology of Plants (eds B.B. Buchanan, W. Gruissem, and R.L. Jones), American Society of Plant Physiologists, Rockville, Maryland, New York, Chapter 24.
7. Taiz, L. and Zeiger, E. (eds). (2006) Secondary metabolites and plant defense, in Plant Physiology, 4th edn, Sinauer Associates, Inc., Chapter 13.
8. Judd, W.S., Campbell, C.S., Kellogg, E.A., Stevens, P.F., and Donoghue, M.J. (2002) Secondary plant compounds, Plant Systematics: A Phylogenetic Approach, Sinauer Associates, New York, Chapter 4.
9. Richards, J.H. and Hendrickson, J.B. (1964) The Biosynthesis of Steroids, Terpenes and Acetogenins, Benjamin, New York.
10. Kuzuyama, T. and Seto, H. (2003) Nat. Prod. Rep., 20, 171-183.
11. Rohmer, M., Seemann, M., Horbach, S., Bringer-Meyer, S., and Sahm, H. (1996) J. Am. Chem. Soc., 118, 2564-2566.
12. Cane, D.E. (1989) Pure Appl. Chem., 61, 493-496.
13. Fischer, N.H., Olivier, E.J., and Fischer, H.D. (1979) The biogenesis and chemistry of sesquiterpene lactones, in Progress Chemistry Organic Natural Products (eds W. Herz, H. Grisebach, and G.W. Kirby), Springer-Verlag, Wien, p. 47.
14. Romo de Vivar, A. (1977) Rev. Latinoam. Quim., 8, 63-73; Chem. Abstr. 1997, 87, 18934.
15. Ruzicka, L. (1953) Experientia, 9, 357-367.
16. Ruzicka, L. (1963) Pure Appl. Chem., 6, 493-523.
17. Cane, D.E. (1989) Pure Appl. Chem., 61, 493-496.
18. Cane, D.E. (1990) Chem. Rev., 90, 1089-1103.
19. Hendrickson, J.B. (1959) Tetrahedron, 7, 82-89.
20. Barton, D.H.R., Bockmann, O.C., and de Mayo, P. (1960) J. Chem. Soc., 2263-2271.
21. Parker, W., Roberts, J.S., and Ramaje, R. (1967) Quart. Rev., 21, 331-363.
22. Herz, W. (1971) Sesquitepene lactones biogenesis, in Pharmacognosy and Phytochemistry (eds H. Wagner and L. Horhammer), Spriner-Verlag, West Berlin and Heidelberg, p. 64;
23. Herz, W. (1977) Israel J. Chem., 16, 32-44.
24. Hanson, J.R. (1979) Terpenoid biosyntheis, in Comprehensive Organic Chemistry (ed. D.H.R. Barton), Academic Press, New York, Chapter 29.
25. Geissman, T.A. (1973) Recent Adv. Phytochem., 6, 65-95.
26. Fischer, N.H., Oliver, E.J., and Fischer, H.D. (1979) Prog. Chem. Org. Nat. Prod., 38, 77-390.
27. Cane, D.E. (1999) Isoprenoids including carotenoids and steroids, in Comprehensive Natural Products Chemistry, vol. 2 (ed. D.E. Cane), Elsevier, Oxford, p. 155;
28. Felicetti, B. and Cane, D.E. (2004) J. Am. Chem. Soc., 126, 7212.
29. Goodwin, T.W. (ed.). (1970) Natural Substances formed Biologically from Mevalonic Acid, Biochemical Symposia, No. 29, Academic Press;
30. MacMillan, J. (1974) Recent aspects on the chemistry and biosynthesis of the Gibberellins. Recent Adv. Phytochem., 7, 1-19.
31. Delgado, G. (2006) Investigación sobre la Química de productos naturales en el Instituto de Química de la UNAM. Estudios iniciales y química de eremofilanos, bisabolanos y sesquiterpenos relacionados, in Química de la Flora Mexicana (ed. A. Romo de Vivar), Instituto de Química, Mexico.
32. Christianson, D.W. (2006) Chem. Rev., 106, 3412-3442.
33. Dewick, P.M. (1999) Nat. Prod. Rep., 16, 97-130;
34. Dewick, P.M. (2002) Nat. Prod. Rep., 19, 181-272.
35. Steel, C.L., Crock, J., Bohlman, J., and Croteau, R. (1998) J. Biol. Chem., 273, 2078.
36. Starcks, C.M., Back, K., Chapell, J., and Noel, J.P. (1997) Science, 277, 1815-1820.
37. Coates, R.M. (1976) Prog. Chem. Org. Nat. Prod., 33, 73-230.
38. Goldsmith, D. (1971) Prog. Chem. Org. Nat. Prod., 29, 363-394.
39. Money, T. (1973) Prog. Org. Chem., 8, 29-77.
40. Allermann, R.K., Young, N.J., Ma, S., Truhlar, D.G., and Gao, J. (2007) J. Am. Chem. Soc., 129, 13008-13013;
41. Chapell, J. (1995) Annu. Rev. Plant Physiol. Plant Mol. Biol., 46, 521-547;
42. McCaskill, D. and Croteau, R. (1995) Planta, 197, 49-56;
43. van Klink, J., Becker, H., Anderson, S., and Boland, W. (2003) Org. Biomol. Chem., 1, 1503-1508.
44. de Kraker, J.-W., Franssen, M.C.F., de Groot, A., König, W.A., and Bouwmeester, H.J. (1998) Plant Physiol., 117, 1381-1392.
45. Fischer, N.H. (1978) Rev. Latinoam. Quím., 9, 41-46.
46. Rao, A.S., Keilkar, G.R., and Bhattacharyya, S.C. (1960) Tetrahedron, 9, 275-283.
47. Fischer, N.H., Mabry, T.J., and Kagan, H.B. (1968) Tetrahedron, 24, 4091-4097.
48. Delgado, G., Tejeda, V., Salas, A., Chavez, M.I., Guzmán, S., Bolaños, A., Aguilar, M.I., Navarro, V., and Villareal, M.L. (1998) J. Nat. Prod., 61, 1082-1085.
49. Benesova, V., Samek, Z., Herout, V., and Sorm, F. (1970) Tetrahedron Lett., 11, 5017-5020.
50. McPhail, A.T., Onan, K.D., Lee, K.H., Ibuka, T., and Huang, H.-Ch. (1974) Tetrahedron Lett., 15, 3203-3206.
51. Fischer, N.H., Seaman, F.C., Wiley, R.A., and Haegele, K.D. (1978) J. Org. Chem, 43, 4984-4987.
52. Gonzalez-Gonzalez, A., Arteaga, J.M., and Breton-Funes, J.L. (1973) Phytochemistry, 12, 2997.
53. For the transformation of epoxygerma-cranolides into guaianolides see: White, E.H. and Winter, R.E.K.,. (1963) Tetrahedron, 19, 137-141;
54. Govindachari, T.R., Josi, B.S., and Kamat, V.N. (1965) Tetrahedron, 21, 1509-1519;
55. Gaissman, T.A. and Ellestad, G.A. (1971) Phytochemistry, 10, 2475-2485;
56. Griffin, T.S., Geissman, T.A., and Winters, T.W. (1971) Phytochemistry, 10, 2487-2495;
57. Irwin, M.A., Lee, K.H., Simpson, R.F., and Geissman, T.A. (1969) Phytochemistry, 8, 2009-2012.
58. For the transformation of 4, 5-epoxy-guaianolide into pseudoguianolides see: Fischer, N.H., Wiley, R.A., and Perry, D.L., (1976) Rev. Latinoamer. Quim, 7, 87-93.
59. Ortega, A. and Maldonado, E. (1989) Heterocycles, 29, 635-638.
60. Takeda, K. (1974) Tetrahedron, 30, 1525-1534.
61. Samek, Z. and Harmatha, J. (1978) Coll. Czech. Chem. Commun., 43, 2779-2799.
62. Parker, W., Roberts, J.S., and Ramaje, R. (1967) Quart. Rev, 21, 331.
63. Fischer, N.H., Wu-Shih, Y.F., Chiari, G., Fronczek, F.R., and Watkins, S.F. (1981) J. Nat. Prod., 44, 104-110.
64. Barquera-Lozada, J.E. and Cuevas, G. (2009) J. Org. Chem., 72, 874-883.
65. Zhao, Y. and Truhlar, D.G. (2004) J. Phys. Chem. A, 108, 6908-6918;
66. Zhao, Y. and Truhlar, D.G. (2008) Acc. Chem. Res., 41, 157-167.
67. Lynch, B.J., Zhao, Y., and Truhlar, D.G. (2003) J. Phys. Chem. A, 107, 1384-1388.
68. Frisch, M.J., Trucks, G.W., Schlegel, H.B., et al.. (2004) Gaussian 03, Revision D. 01, Gaussian, Inc., Wallingford CT
69. Pawar, D.M., Smith, S.V., Mark, H.L., Odom, R.M., and Noe, E.A. (1998) J. Am. Chem. Soc., 120, 10715-10720.
70. Fernández-Alonso, M.C., Asensio, J.L., Cañada, F.J., Jiménez-Barbero, J., and Cuevas, G. (2003) Chem. Phys. Chem., 4, 748-753.
71. Fernández-Alonso, M.C., Cañada, J., Jiménez-Barbero, J., and Cuevas, G. (2005) Chem. Phys. Chem., 6, 671-681.
72. Juaristi, E. and Cuevas, G. (2008) Acc. Chem. Res., 40, 961-970.
73. Laube, T. (1995) Acc. Chem. Res., 28, 399-405.
74. Carpenter, J.E. and Weinhold, F. (1988) J. Mol. Struct. (THEOCHEM), 169, 41-62;
75. Foster, J.P. and Weinhold, F. (1980) J.Am. Chem. Soc., 102, 7211;
76. Carpenter, J.E. (1987) PhD Thesis, University of Wisconsin, Madison, WI.
77. Reed, A.E. and Weinhold, F. (1983) J. Chem. Phys., 78, 4066-4073;
78. Reed, A.E. and Weinhold, F. (1985) J. Chem. Phys., 83, 1736-1740;
79. Reed, A.E., Weinstock, R.B., and Weinhold, F. (1985) J. Chem. Phys., 83, 735-746;
80. Reed, A.E., Curtiss, L.A., and Weinhold, F. (1988) Chem. Rev., 88, 899-926.
81. Smith, M.B. and March, J. (2007) March's Advanced Organic Chemistry: Reactions, Mechanisms and Structure, John Wiley & Sons Inc., Hoboken, p. 1581.
82. Carey, F.C. and Sundberg, R.J. (1990) Advanced Organic Chemistry (Part A), Plenum, p. 317.
83. Breneman, C.M. and Wiberg, K.B. (1990) J. Comput. Chem., 11, 361-373.
84. Deslongchamps, P. (1983) Stereoelectronic Effects in Organic Chemistry, Pergamon Press, Oxford;
85. Szarek, W.A. and Horton, D. (eds). (1979) Anomeric Effect: Origin and Consequences (ACS Symposium Series,No. 87), American Chemical Society, Washington DC;
86. Kirby, A.J. (1983) The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer, New York;
87. Juaristi, E. and Cuevas, G. (1992) Tetrahedron, 48, 5019-5087;
88. Thatcher, G.R.J. (ed.). (1993) The Anomeric and Associated Stereoelectronic Effects, American Chemical Society, Washington DC;
89. Graczyk, P.P. and Mikolajczyk, M. (1994) Top. Stereochem., 21, 159-349;
90. Juaristi, E. and Cuevas, G. The Anomeric Effect, CRC Press, Boca Raton, FL;
91. Chattopadhyaya, J. (1999) Stereoelectronic Effects in Nucleosides and their Structural Implications, Uppsala University Press, Uppsala;
92. Perrin, C.L. (2002) Acc. Chem. Res., 35, 28-34.
93. Zhao, Y., Schultz, N.E., and Truhlar, D.G. (2006) J. Chem. Theory Comput., 2, 364.
94. Tantillo, D.J. (2008) J. Phys. Org. Chem., 21, 561-570.
95. Gutta, P. and Tantillo, D.J. (2006) J. Am. Chem. Soc., 128, 6172-6179.
96. Vrcek, I.V., Vrcek, V., and Siehl, H. (2002) J. Phys. Chem. A, 106, 1604-1611.
97. Vrcek, V., Vrcek, I.V., and Siehl, H. (2006) J. Phys. Chem. A, 110, 1868-1874.