Probing eudesmane cation-π interactions in catalysis by aristolochene synthase with non-canonical amino acids

Journal of the American Chemical Society

Volumn 133, Issue 35, 2011, Pages 13906-13909

  Faraldos, Juan A ^a   Antonczak, Alicja K ^a   González, Verónica ^a   Fullerton, Rebecca ^a   Tippmann, Eric M ^a   Allemann, Rudolf K ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINO ACID; DOUBLE BONDS; ELECTRONWITHDRAWING; GERMACRENE; GOOD CORRELATIONS; INTERACTION ENERGIES; MUTANT ENZYMES; PENICILLIUM ROQUEFORTI; PROGRESSIVE ACCUMULATION; PROTEINOGENIC; SUBSTITUTED BENZENES; SYNTHASE CATALYSIS; SYNTHASES;

AMINO ACIDS; BENZENE; CATALYSIS; POSITIVE IONS; REACTION INTERMEDIATES; STABILIZATION;

BENZENE REFINING;

ARISTOLOCHENE SYNTHASE; AROMATIC AMINO ACID; BENZENE; CATION; EUDESMANE DERIVATIVE; GERMACRENE A; PHENYLALANINE; SODIUM ION; SYNTHETASE; TERPENOID DERIVATIVE; TRYPTOPHAN; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; CATION EXCHANGE; CHEMICAL BOND; ELECTRON; ENZYME ACTIVE SITE; ENZYME MECHANISM; PENICILLIUM ROQUEFORTI; PROTON TRANSPORT; X RAY CRYSTALLOGRAPHY;

AMINO ACIDS; CATIONS; ISOMERASES; MODELS, MOLECULAR; MUTATION; PENICILLIUM; SESQUITERPENES; SESQUITERPENES, EUDESMANE; SESQUITERPENES, GERMACRANE;

EID: 80052324597     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja205927u     Document Type: Article

References (61)

1. Hohn, T. M.; Plattner, R. D. Arch. Biochem. Biophys. 1989, 272, 137-143
2. Cane, D. E.; Wu, Z.; Proctor, R. H.; Hohn, T. M. Arch. Biochem. Biophys. 1993, 304, 415-419
3. Cane, D. E.; Prabhakaran, P. C.; Salaski, E. J.; Harrison, P. H. M.; Noguchi, H.; Rawlings, B. J. J. Am. Chem. Soc. 1989, 111, 8914-8916
4. Cane, D. E.; Kang, I. Arch. Biochem. Biophys. 2000, 376, 354-364
5. Vogeli, U.; Freeman, J. W.; Chappell, J. Plant Physiol. 1990, 93, 182-187
6. Rising, K. A.; Starks, C. M.; Noel, J. P.; Chappell, J. J. Am. Chem. Soc. 2000, 122, 1861-1866
7. Jelen, H. H. J. Agric. Food Chem. 2002, 50, 6569-6574
8. Whitehead, I. M.; Threlfall, D. R.; Ewing, D. F. Phytochemistry 1989, 28, 775-779
9. Whitehead, I. M.; Ewing, D. F.; Threlfall, D. R.; Cane, D. E.; Prabhakaran, P. C. Phytochemistry 1990, 29, 479-482
10. Miller, D. J.; Yu, F. L.; Allemann, R. K. ChemBioChem 2007, 8, 1819-1825
11. Faraldos, J. A.; Zhao, Y. X.; OMaille, P. E.; Noel, J. P.; Coates, R. M. ChemBioChem 2007, 8, 1826-1833
12. Miller, D. J.; Yu, F. L.; Allemann, R. K Org. Biomol. Chem. 2009, 7, 962-975
13. Cane, D. E.; Tsantrizos, Y. S. J. Am. Chem. Soc. 1996, 118, 10037-10040
14. Cane, D. E.; Bryant, C. J. Am. Chem. Soc. 1994, 116, 12063-12064
15. Faraldos, J. A.; Kariuki, B.; Allemann, R. K. J. Org. Chem. 2010, 75, 1119-1125
16. Faraldos, J. A.; Alleman, R. K. Org. Lett. 2011, 13, 1202-1205
17. Cane, D. E.; Prabhakaran, P. C.; Oliver, J. S.; Mc Ilwaine, D. B. J. Am. Chem. Soc. 1990, 112, 3209-3210
18. Calvert, M. J.; Ashton, P. R.; Allemann, R. K. J. Am. Chem. Soc. 2002, 124, 11636-11641
19. Deligeorgopoulou, A.; Taylor, S. E.; Forcat, S.; Allemann, R. K. Chem. Commun. 2003, 2162-2163
20. Forcat, S.; Allemann, R. K. Chem. Commun. 2004, 2094-2095
21. Felicetti, B.; Cane, D. E. J. Am. Chem. Soc. 2004, 126, 7212-7221
22. Caruthers, J. M.; Kang, I.; Rynkiewicz, M. J.; Cane, D. E.; Christianson, D. W. J. Biol. Chem. 2000, 275, 25533-25539
23. Shishova, E. Y.; Di Costanzo, L.; Cane, D. E.; Christianson, D. W. Biochemistry 2007, 46, 1941-1951
24. Shishova, E. Y.; Yu, F. L.; Miller, D. J.; Faraldos, J. A.; Zhao, Y. X.; Coates, R. M.; Allemann, R. K.; Cane, D. E.; Christianson, D. W. J. Biol. Chem. 2008, 283, 15431-15439
25. Cane, D. E. Chem. Rev. 1990, 90, 1089-1103
26. Davis, E. M.; Croteau, R. Top. Curr. Chem. 2000, 209, 53-95
27. Tantillo, D. E. Nat. Prod. Rep. 2011, 28, 1035-1053
28. Christianson, D. W. Chem. Rev. 2006, 106, 3412-3442
29. Dougherty, D. A.; Stauffer, D. A. Science 1990, 250, 1558-1560
30. Dougherty, D. A. Science 1996, 271, 163-168
31. Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324
32. Gavillan, J. P.; Dougherty, D. A. Proc. Natl. Acad. Sci. U.S.A. 1999, 93, 10566-10571
33. Zacharias, N.; Dougherty, D. A. Trends Pharmacol. Sci. 2002, 23, 281-287
34. Gromiha, M. M.; Santhosh, C.; Amad, S. Biol. Macromol. 2004, 34, 201-211
35. Comprehensive Supramolecular Chemistry; Atwood, J. L.; Davies, J. E. D.; MacNicol, D. D.; Vogtle, F.; Lehn, J.-M., Eds.; Elsevier Science Ltd.: Oxford, 1996.
36. Cubero, E.; Luque, F. J.; Ozorzo, M. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 5976-5980
37. Tsuzuki, S.; Yoshida, M.; Uchimaru, T.; Mikami, M. J. Phys. Chem. A 2001, 105, 769-773
38. Tsuzuki, S.; Mikami, M.; Yamada, S. J. Am. Chem. Soc. 2007, 129, 8656-8662
39. Soteras, I.; Ozorzo, M.; Luque, F. J. Phys. Chem. Chem. Phys. 2008, 10, 2616-2624
40. Sandifer, R. M.; Thompson, M. D.; Gaughan, R. G.; Poulter, C. D. J. Am. Chem. Soc. 1982, 104, 7376-7378
41. Croteau, R.; Wheeler, C. J.; Aksela, R.; Oehlschlager, A. C. J. Biol. Chem. 1986, 261, 7257-7263
42. Poulter, C. D.; Capson, T. L.; Thompson, M. D.; Bard, R. S. J. Am. Chem. Soc. 1989, 111, 3734-3739
43. McGeady, P.; Pyun, H. J.; Coates, R. M.; Croteau, R. Arch. Biochem. Biophys. 1992, 299, 63-72
44. Cane, D. E.; Yang, G. H.; Coates, R. M.; Pyun, H. J.; Hohn, T. M. J. Org. Chem. 1992, 57, 3454-3462
45. Koohang, A.; Coates, R. M.; Owen, D.; Poulter, C. D. J. Org. Chem. 1999, 64, 6-7
46. Peters, R. J.; Ravn, M. M.; Coates, R. M.; Croteau, R. B. J. Am. Chem. Soc. 2001, 123, 8974-8978
47. Ravn, M. M.; Peters, R. J.; Coates, R. M.; Croteau, R. J. Am. Chem. Soc. 2002, 124, 6998-7006
48. Roy, A.; Roberts, F. G.; Wilderman, P. R.; Zhou, K.; Peters, R. J.; Coates, R. M. J. Am. Chem. Soc. 2007, 129, 12453-12460
49. Koohang, A.; Bailey, J. L.; Coates, R M.; Erickson, H. K.; Owen, D.; Poulter, C. D. J. Org. Chem. 2010, 75, 4769-4777
50. Whittington, D. A.; Wise, M. L.; Urbansky, M.; Coates, R. M.; Croteau, R. B.; Christianson, D. W. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 15375-15380
51. Vedula, L. S.; Rynkiewicz, M. J.; Pyun, H.-J.; Coates, R. M.; Cane, D. E.; Christianson, D. W. Biochemistry 2005, 44, 6153-6163
52. Christianson, D. W. Curr. Opin. Chem. Biol. 2008, 12, 141-150
53. Zhou, K.; Peters, R. J. Chem. Commun. 2011, 47, 4074-4080
54. Mecozzi, S.; West, A. P.; Dougherty, D. A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 10566-10571
55. Mecozzi, S.; West, A. P.; Dougherty, D. A. J. Am. Chem. Soc. 1996, 118, 2307-2308
56. Wheeler, S. E.; Houk, K. N. J. Am. Chem. Soc. 2009, 131, 3126-3127
57. Marshall, S, M.; Steele, R. P.; Thanthiriwatte, K. S.; Sherrill, C. D. J. Phys. Chem. A 2009, 113, 13628-13632
58. Richards, F. M. Annu. Rev. Biophys. Bioeng. 1977, 6, 151-176
59. Wan, L.; Brock, A.; Herberich, B.; Schultz, P. G. Science 2001, 292, 498-500
60. Starks, C. M.; Back, K.; Chappell, J.; Noel, J. P. Science 1997, 277, 1815-1820
61. Morikubo, N.; Fukada, Y.; Ohtake, K.; Shinya, N.; Kiga, D.; Sakamoto, K.; Asanuma, M.; Hirota, H.; Yokoyama, S.; Hoshino, T. J. Am. Chem. Soc. 2006, 128, 13184-13194