Stereochemistry and deuterium isotope effects associated with the cyclization-rearrangements catalyzed by tobacco epiaristolochene and hyoscyamus premnaspirodiene synthases, and the chimeric CH4 hybrid cyclase

Archives of Biochemistry and Biophysics

Volumn 448, Issue 1-2, 2006, Pages 31-44

  Schenk, David J ^a   Starks, Courtney M ^b   Manna, Kathleen Rising ^c   Chappell, Joe ^c   Noel, Joseph P ^b   Coates, Robert M ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b HOWARD HUGHES MEDICAL INSTITUTE   (United States)

^c UNIVERSITY OF KENTUCKY   (United States)

Author keywords

Carbocations; Cyclizations; Deuterium labeling; Enzyme mechanisms; Eremophilanes; Germacrane; Isotope effects; Rearrangements; Sesquiterpenes; Spirovetivane; Stereochemistry

Indexed keywords

CYCLOHEXENE DERIVATIVE; DEUTERIUM; FARNESYL DIPHOSPHATE; GERMACRENE D; HYDROCARBON; HYOSCYAMINE; ISOTOPE; PROTON;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CATALYSIS; CHEMICAL BOND; CONFORMATIONAL TRANSITION; CYCLIZATION; ENZYME MECHANISM; GAS CHROMATOGRAPHY; HYOSCYAMUS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY;

CARBON-CARBON LYASES; CARBON-NITROGEN LIGASES; CATALYSIS; DEUTERIUM; HYOSCYAMUS; ISOTOPE LABELING; MAGNETIC RESONANCE SPECTROSCOPY; SESQUITERPENES; STEREOISOMERISM; TOBACCO;

HYOSCYAMUS; NICOTIANA TABACUM;

EID: 33646153062     PISSN: 00039861     EISSN: 10960384     Source Type: Journal    
DOI: 10.1016/j.abb.2005.09.002     Document Type: Article

References (64)

1. D.E. Cane in: D. Barton, K. Nakanishi, O. Meth-Cohn, Eds. Comprehensive Natural Products Chemistry, vol. 2; D.E. Cane, Ed.; Elsevier, Amsterdam, (1999), Chap. 6.
2. Cane D.E. Chem. Rev. 90 (1990) 1089-1103
3. Brooks C.J.W., and Watson D.G. Nat. Prod. Rep. 2 (1985) 427-460
4. Brooks C.J.W., and Watson D.G. Nat. Prod. Rep. 8 (1991) 367-390
5. Sharma R.P., and Salunkhe D.K. Mycotoxins and Phytoalexins (1991), CRC Press, Boca Raton
6. Baker F.C., and Brooks C.J.W. Phytochemistry 15 (1976) 689-694
7. Hoyano Y., Stoessel A., and Stothers J.B. Can. J. Chem. 58 (1980) 1894-1896
8. Whitehead I.M., Threlfall D.R., and Ewing D.F. Phytochemistry 28 (1989) 775-779
9. Whitehead I.M., Ewing D.F., Threlfall D.R., Cane D.E., and Prabhakaran P.C. Phytochemistry 29 (1990) 479-482
10. Birnbaum G.I., Stoessl A., Grover S.H., and Stothers J.B. Can. J. Chem. 52 (1974) 993-1005
11. Zhao Y., Schenk D.J., Takahashi S., Chappell J., and Coates R.M. J. Org. Chem. 69 (2004) 7428-7435
12. Takahashi S., Zhao Y., O' Maille P.E., Greenhagen B.T., Noel J.P., Coates R.M., and Chappell J. J. Biol. Chem 280 (2005) 3686-3696
13. Murai A., Yoshizawa Y., Katsui N., Sato S., and Masamune T. Chem. Lett. (1986) 771-772
14. Murai A., Sato S., Osada A., Katsui N., and Masamune T. J. Chem. Soc. Chem. Commun. (1982) 32-33
15. Whitehead I.M., Atkinson A.L., and Threlfall D.R. Planta 182 (1990) 81-88
16. Rao C.B., Raju G.V.S., and Krishna P.G. Ind. J. Chem. Sect. B 21B (1982) 267-268
17. Hwu J.R., and Wetzel J.M. J. Org. Chem. 57 (1992) 922-928
18. Zee S.H., Chou S.Y., and Chinese J. Chem. Soc. (Taipei, Taiwan) 37 (1990) 191-195
19. Back K., and Chappell J. J. Biol. Chem. 270 (1995) 7375-7381
20. Back K., Yin S., and Chappell J. Arch. Biochem. Biophys. 315 (1994) 527-532
21. Back K., and Chappell J. Proc. Natl. Acad. Sci. USA 93 (1996) 6841-6845
22. Mathis J.R., Back K., Starks C., Noel J., Poulter C.D., and Chappell J. Biochemistry 36 (1997) 8340-8348
23. Starks C.M., Back K., Chappell J., and Noel J.P. Science 277 (1997) 1815-1820
24. Rising K.A., Starks C.M., Noel J.P., and Chappell J. J. Am. Chem. Soc. 122 (2000) 1861-1866
25. Cane D.E., Prabhakaran P.C., Oliver J.S., and McIlwaine D.B. J. Am. Chem. Soc. 112 (1990) 3209-3210
26. Cane D.E., Prabhakaran P.C., Salaski E.J., Harrison P.H.M., Noguchi H., and Rawlings B.J. J. Am. Chem. Soc. 111 (1989) 8914-8916
27. Cane D.E., and Tsantrizos Y.S. J. Am. Chem. Soc. 118 (1996) 10037-10040
28. Still C.W., Kahn M., and Mitra A. J. Org. Chem. 43 (1978) 2923-2925
29. Morimoto Y., Matsuda F., and Shirahama H. Tetrahedron 52 (1996) 10609-10630
30. Yee N.K.N., and Coates R.M. J. Org. Chem. 57 (1992) 4598-4608
31. Ravn M.M., Jin A.Q., and Coates R.M. Eur. J. Org. Chem. (2000) 1401-1410
32. Jin Q., Williams D.C., Hezari M., Croteau R., and Coates R.M. J. Org. Chem. 70 (2005) ASAP
33. Clarke H.T., and Hartman W.W. Org. Synth. Coll. 1 (1993) 233-234
34. Still W.C., and Gennari C. Tetrahedron Lett. 24 (1983) 4405-4408
35. Coates R.M., Ley D.A., and Cavender P.L. J. Org. Chem. 43 (1978) 4915-4922
36. Welch S.C., and Walters M.E.J. J. Org. Chem. 43 (1978) 4797-4799
37. D.J. Schenk, Ph.D Dissertation, University of Illinois, Urbana, IL, 2000; Diss. Abstr. B; Order No. DA 9990130, 61(2000) 5334.
38. Corey E.J., Cane D.E., and Libit L.J. J. Am. Chem. Soc. 93 (1971) 7016-7021
39. Corey E.J., and Achiwa K.J. Org. Chem. 34 (1969) 3667-3668
40. Davisson V.J., Woodside A.B., Neal T.R., Stremler K.E., Muehlbacker M., and Poulter C.D. J. Org. Chem. 51 (1986) 4768-4779
41. Gerlach H., and Zagalak B.J. J. Chem. Soc. Chem. Commun. (1973) 274-275
42. Gerlach H., Kappes D., Boeckman Jr. R.K., and Maw G.N. Org. Synth. Coll. 9 (1998) 151-154
43. Crandall J.K., and Pradat C. J. Org. Chem. 50 (1985) 1327-1329
44. Collington E.W., and Meyers A.I. J. Org. Chem. 36 (1971) 3044-3045
45. Woodside A.B., Huang Z., and Poulter C.D. Org. Synth. Coll. 8 (1993) 616-620
46. Schowen K.B., and Schowen R.L. Methods Enzymol. 87 (1982) 551-606
47. M.M. Ravn, Ph.D. Thesis, University of Illinois, Urbana, IL, (2000).
48. Cane D.E., Oliver J.S., Harrison P.H.M., Abell C., Hubbard B.R., Kane C.T., and Lattman R. J. Am. Chem. Soc. 112 (1990) 4513-4524
49. Ravn M.M., Coates R.M., Jetter R., and Croteau R.B. J. Chem. Soc. Chem. Commun. (1998) 21-22
50. Lin X., Hezari M., Koepp A.E., Floss H.G., and Croteau R. Biochemistry 35 (1996) 2968-2977
51. Williams D.C., Carroll B., Jin Q., Rithner C., Lenger S.R., Floss H.G., Coates R.M., Williams R.M., and Croteau R. Chem. Biol. 7 (2000) 969-977
52. Pyun H.-J., Coates R.M., Wagschal K.C., McGeady P., and Croteau R.B. J. Org. Chem. 58 (1993) 3998-4009
53. Suga T., Hiraga Y., Mie A., and Izumi S. J. Chem. Soc. Chem. Commun. (1992) 1556-1558
54. Leopold M.F., Epstein W.W., and Grant D.M. J. Am. Chem. Soc. 110 (1988) 616-617
55. Birnbaum G.I., Huber C.P., Post M.L., Stothers J.B., Robinson J.R., Stoessel A., and Ward E.W.B. J. Chem. Soc. Chem. Commun. (1976) 330-331
56. L. Botta, Ph.D. Thesis, ETH, Zurich, Switzerland, (1968).
57. L. Guglielmietta, Ph.D. Thesis, ETH, Zurich, Switzerland, (1962).
58. Wagschal K.C., Pyun H.-J., Coates R.M., and Croteau R. Arch. Biochem. Biophys. 308 (1994) 477-487
59. Streitwieser Jr. A. Solvolytic Displacement Reactions (1962), McGraw-Hill, New York pp. 98-102
60. Shiner Jr. V.J. J. Am. Chem. Soc. 75 (1953) 2925-2929
61. Walsh C. Enzymatic Reaction Mechanisms (1979), Freeman, San Francisco pp. 118-123
62. Adio A.M., Paul C., Tesso H., Kloth P., and König W.A. Tetrahedron Asymmetr. 15 (2004) 1631-1635
63. Rickert K.W., and Klinman J.P. Biochemistry 38 (1999) 12218-12228
64. Adediran S.A., and Pratt R.F. Biochemistry 38 (1999) 1469-1477