Does the TauD enzyme always hydroxylate alkanes, while an analogous synthetic non-heme reagent always desaturates them?

Journal of the American Chemical Society

Volumn 133, Issue 2, 2011, Pages 176-179

  Usharani, Dandamudi ^a   Janardanan, Deepa ^a   Shaik, Sason ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE OXIDATION; CYCLOHEXADIENES; DESATURASE; DIOXYGENASES; HYDROXYLASES; INTRINSIC REACTIVITY; OXOIRON; REACTION PATHWAYS; SELECTION RULES; SELECTIVE CATALYSTS; SPIN STATE;

AMINO ACIDS; ETHANE; OLEFINS; PORPHYRINS; SPHERES; SPIN DYNAMICS;

ENZYMES;

ALCOHOL; ALKENE; CYCLOHEXANE; CYCLOPENTANE; ETHANE; IRON HYDROTRIS(3,5 DIPHENYLPYRAZOL 1 YL)BORATE BENZOATE; OXYGENASE; REAGENT; TAURINE ALPHA KETOGLUTARASE DIOXYGENASE; TAURINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; HYDROXYLATION; OXIDATION; REACTION ANALYSIS;

ALKANES; HYDROXYLATION; IRON COMPOUNDS; MIXED FUNCTION OXYGENASES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 78651400485     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja107339h     Document Type: Article

References (39)

1. Acc. Chem. Res. 2007, 40 (7), 465 - 634 (special issue on Dioxygen Activation by Metalloenzymes and Models).
2. Krebs, C., Fujimori, D. G., Walsh, C. T., and Bollinger, M. J., Jr. Acc. Chem. Res. 2007, 40, 484-492
3. Nam, W. Acc. Chem. Res. 2007, 40, 522-531
4. Kim, C., Dong, Y., and Que, L., Jr. J. Am. Chem. Soc. 1997, 119, 3635-3636
5. Xue, G., de Hont, R., Münck, E., and Que, L., Jr. Nat. Chem. 2010, 2, 400-405
6. Zhou, J., Kelly, W. L., Bachmann, B. O., Gunsior, M., Townsend, C. A., and Solomon, E. I. J. Am. Chem. Soc. 2001, 123, 7388-7398
7. Jin, Y. and Lipscomb, J. D. J. Biol. Inorg. Chem. 2001, 6, 717-725
8. Mukherjee, A., Martinho, M., Bominaar, E. L., Münck, E., and Que, L., Jr. Angew. Chem., Int. Ed. 2009, 48, 1780-1783
9. Groves, J. T. J. Chem. Educ. 1985, 62, 928-931
10. 2-core desaturases, see, for example: Fox, B. G., Lyle, K. S., and Rogge, C. E. Acc. Chem. Res. 2004, 37, 421-429
11. Buist, P. H. Nat. Prod. Rep. 2004, 21, 249-262
12. Behrouzian, B. and Buist, P. H. Curr. Opin. Chem. Biol. 2002, 6, 577-582
13. For reviews of this bifurcation in P450, see, for example: Akhtar, M. and Wright, J. N. Nat. Prod. Rep. 1991, 8, 527-551
14. Guengerich, F. P. Chem. Res. Toxicol. 2001, 14, 611-650
15. Ortiz de Montellano, P. R. Trends Pharmacol. Sci. 1989, 10, 354-359
16. For computational data showing proton-coupled electron transfer in P450, see: Kumar, D., de Visser, S. P., and Shaik, S. J. Am. Chem. Soc. 2004, 126, 5072-5073
17. Hackett, J. C., Brueggemeier, R. W., and Hadad, C. M. J. Am. Chem. Soc. 2005, 127, 5224-5237
18. Kumar, D., Tahsini, L., de Visser, S. P., Kang, H. Y., Kim, S. J., and Nam, W. J. Phys. Chem. A 2009, 113, 11713-11722
19. Hull, J. F., Balcells, D., Sauer, E. L. O., Raynaud, C., Brudvig, G. W., Crabtree, R. H., and Eisenstein, O. J. Am. Chem. Soc. 2010, 132, 7605-7616
20. For example, see: Shaik, S., Hirao, H., and Kumar, D. Acc. Chem. Res. 2007, 40, 532-542
21. Janardanan, D., Wang, Y., Schyman, P., Que, L., Jr., and Shaik, S. Angew. Chem., Int. Ed. 2010, 49, 3342-3345
22. Johansson, A. J., Blomberg, M. R., and Siegbahn, P. E. M. J. Phys. Chem. C 2007, 111, 12397-12406
23. Latifi, R., Bagherzadeh, M., and de Visser, S. P. Chem. - Eur. J. 2009, 15, 6651-6662
24. Godfrey, E., Porro, C. S., and de Visser, S. P. J. Phys. Chem. A 2008, 112, 2464-2468
25. Ye, S. and Neese, F. Curr. Opin. Chem. Biol. 2009, 13, 89-98
26. Geng, C., Ye, S., and Neese, F. Angew. Chem., Int. Ed. 2010, 49, 5717-5720
27. Bernasconi, L., Louwerse, M. J., and Baerends, E. J. Eur. J. Inorg. Chem. 2007, 3023-3033
28. For a recent review of two-state reactivity, see: Schwarz, H. Int. J. Mass. Spectrom. 2004, 237, 75-105
29. Ha, E. H., Ho, R. Y. N., Kisiel, J. F., and Valentine, J. S. Inorg. Chem. 1995, 34, 2265-2266
30. Gonzalez, C. and Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154-2161
31. Frisch, M. J.; et al. Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
32. Jaguar, version 7.6; Schrödinger, LLC: New York, 2008.
33. Grimme, S. J. Comput. Chem. 2006, 27, 1787-1799
34. Mayer, J. M. Acc. Chem. Res. 1998, 31, 441-450
35. Shaik, S., Lai, W. Z., and Chen, H. Acc. Chem. Res. 2010, 43, 1154-1165
36. Hirao, H., Kumar, D., Que, L., Jr., and Shaik, S. J. Am. Chem. Soc. 2006, 128, 8590-8606
37. Decker, A., Rohde, J.-U., Klinker, E. J., Wong, S. D., Que, L., Jr., and Solomon, E. I. J. Am. Chem. Soc. 2007, 129, 15983-15996
38. Wang, Y. and Han, K. J. Biol. Inorg. Chem. 2010, 15, 351-359
39. Bukowski, M. R., Kohentop, K. D., Stubna, A., Bominaar, E. L., Halfen, J. A., Münck, E., Nam, W., and Que, L., Jr. Science 2005, 310, 1000-1002