Mechanism of the P450-Catalyzed Oxidative Cyclization in the Biosynthesis of Griseofulvin

ACS Catalysis

Volumn 6, Issue 7, 2016, Pages 4506-4511

  Grandner, Jessica M ^a   Cacho, Ralph A ^b   Tang, Yi ^a,b   Houk, K N ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b University of California   (United States)

Author keywords

computations; DFT; griseofulvin; mechanism; O H abstraction; p450

Indexed keywords

ABSTRACTING; ANTIFUNGAL AGENTS; ANTIVIRAL AGENTS; BIOCHEMISTRY; BIOSYNTHESIS; CALCULATIONS; CATALYSIS; DENSITY FUNCTIONAL THEORY; MECHANISMS;

GRISEOFULVIN; H-ABSTRACTION; NATURAL PRODUCTS; OXIDATIVE CYCLIZATION; P450;

CYCLIZATION;

EID: 84977080529     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.6b01068     Document Type: Article

References (50)

1. Ho, Y.-S.; Duh, J.-S.; Jeng, J.-H.; Wang, Y.-J.; Liang, Y.-C.; Lin, C.-H.; Tseng, C.-J.; Yu, C.-F.; Chen, R.-J.; Lin, J.-K. Int. J. Cancer 2001, 91, 393-401 10.1002/1097-0215(200002)9999:9999<::AID-IJC1070>3.0.CO;2-#
2. Camden, J. B. (Procter & Gamble Co.). International Patent WO9705870, 1997.
3. Panda, D.; Rathinasamy, K.; Santra, M. K.; Wilson, L. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 9878-9883 10.1073/pnas.0501821102
4. Oda, T. J. Antibiot. 2006, 59, 114-116 10.1038/ja.2006.17
5. Raab, M. S.; Breitkreutz, I.; Anderhub, S.; Rønnest, M. H.; Leber, B.; Larsen, T. O.; Weiz, L.; Konotop, G.; Hayden, P. J.; Podar, K.; Fruehauf, J.; Nissen, F.; Mier, W.; Haberkorn, U.; Ho, A. D.; Goldschmidt, H.; Anderson, K. C.; Clausen, M. H.; Krämer, A. Cancer Res. 2012, 72, 5374-5385 10.1158/0008-5472.CAN-12-2026
6. Jin, H.; Yamashita, A.; Maekawa, S.; Yang, P.; He, L. M.; Takayanagi, S.; Wakita, T.; Sakamoto, N.; Enomoto, N.; Ito, M. Hepatol. Res. 2008, 38, 909-918 10.1111/j.1872-034X.2008.00352.x
7. Petersen, A. B.; Rønnest, M. H.; Larsen, T. O.; Clausen, M. H. Chem. Rev. 2014, 114, 12088-12107 10.1021/cr400368e
8. Chooi, Y.-H.; Cacho, R.; Tang, Y. Chem. Biol. 2010, 17, 483-494 10.1016/j.chembiol.2010.03.015
9. Cacho, R. A.; Chooi, Y.-H.; Zhou, H.; Tang, Y. ACS Chem. Biol. 2013, 8, 2322-2330 10.1021/cb400541z
10. Frisch, M. J.; Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford CT, 2009. (see Supplemental Information for full reference).
11. Becke, A. D. Phys. Rev. A: At., Mol., Opt. Phys. 1988, 38, 3098-3100 10.1103/PhysRevA.38.3098
12. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652 10.1063/1.464913
13. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter Mater. Phys. 1988, 37, 785-789 10.1103/PhysRevB.37.785
14. Zhao, Y.; Truhlar, D. G. Phys. Chem. Chem. Phys. 2008, 10, 2813-2818 10.1039/b717744e
15. Ribeiro, R. F.; Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2011, 115, 14556-14562 10.1021/jp205508z
16. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104 10.1063/1.3382344
17. Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comput. Chem. 2011, 32, 1456-1465 10.1002/jcc.21759
18. Schyman, P.; Lai, W.; Chen, H.; Wang, Y.; Shaik, S. J. Am. Chem. Soc. 2011, 133, 7977-7984 10.1021/ja201665x
19. Kim, D. E.; Chivian, D.; Baker, D. Nucleic Acids Res. 2004, 32, W526-W531 10.1093/nar/gkh468
20. Bradley, P.; Malmström, L.; Qian, B.; Schonbrun, J.; Chivian, D.; Kim, D. E.; Meiler, J.; Misura, K. M. S.; Baker, D. Proteins: Struct., Funct., Genet. 2005, 61, 128-134 10.1002/prot.20729
21. Trott, O.; Olson, A. J. J. Comput. Chem. 2010, 31, 455-461 10.1002/jcc.21334
22. Shaik, S.; Cohen, S.; Wang, Y.; Chen, H.; Kumar, D.; Thiel, W. Chem. Rev. 2010, 110, 949-1017 10.1021/cr900121s
23. de Visser, S. P.; Shaik, S. J. Am. Chem. Soc. 2003, 125, 7413-7424 10.1021/ja034142f
24. Shaik, S.; Milko, P.; Schyman, P.; Usharani, D.; Chen, H. J. Chem. Theory Comput. 2011, 7, 327-339 10.1021/ct100554g
25. Bathelt, C. M.; Ridder, L.; Mulholland, A. J.; Harvey, J. N. J. Am. Chem. Soc. 2003, 125, 15004-15005 10.1021/ja035590q
26. Bathelt, C. M.; Ridder, L.; Mulholland, A. J.; Harvey, J. N. Org. Biomol. Chem. 2004, 2, 2998-3005 10.1039/B410729B
27. Bathelt, C. M.; Mulholland, A. J.; Harvey, J. N. J. Phys. Chem. A 2008, 112, 13149-13156 10.1021/jp8016908
28. Foster, J. P.; Weinhold, F. J. Am. Chem. Soc. 1980, 102, 7211-7218 10.1021/ja00544a007
29. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926 10.1021/cr00088a005
30. Farokhi, S. A.; Nandibewoor, S. T. Tetrahedron 2003, 59, 7595-7602 10.1016/S0040-4020(03)01148-7
31. Shimpi, R.; Fadat, R.; Janarao, D. M.; Farooqui, M. J. Chem. Pharm. Res. 2014, 6, 1011-1019
32. Singh, H. S.; Singh, V. P.; Pandey, D. P. Monatsh. Chem. 1979, 110, 1455-1460 10.1007/BF00938301
33. Day, A. C.; Nabney, J.; Scott, A. I. Proc. Chem. Soc. 1960, 284
34. Day, A. C.; Nabney, J.; Scott, A. I. J. Chem. Soc. 1961, 4067 10.1039/jr9610004067
35. Kuo, C. H.; Hoffsommer, R. D.; Slates, H. L.; Taub, D.; Wendler, N. L. Chem. Ind. 1961, 1627
36. Tian, Z.; Kass, S. R. J. Am. Chem. Soc. 2008, 130, 10842-10843 10.1021/ja802088u
37. Gesell, A.; Rolf, M.; Ziegler, J.; Díaz Chávez, M. L.; Huang, F. C.; Kutchan, T. M. J. Biol. Chem. 2009, 284, 24432-24442 10.1074/jbc.M109.033373
38. Holding, A. N.; Spencer, J. B. ChemBioChem 2008, 9, 2209-2214 10.1002/cbic.200800303
39. Wang, Y.; Yang, C.; Wang, C.; Han, K.; Shaik, S. ChemBioChem 2007, 8, 277-281 10.1002/cbic.200600510
40. Barckholtz, C.; Barckholtz, T. A.; Hadad, C. M. J. Am. Chem. Soc. 1999, 121, 491-500 10.1021/ja982454q
41. Klein, E.; Lukeš, V. J. J. Mol. Struct.: THEOCHEM 2006, 767, 43-50 10.1016/j.theochem.2006.04.017
42. Nam, P.-C.; Nguyen, M. T.; Chandra, A. K. J. Phys. Chem. A 2005, 109, 10342-10347 10.1021/jp0534030
43. Guengerich, F. P. J. Labelled Compd. Radiopharm. 2013, 56, 428-431 10.1002/jlcr.3031
44. Shinkyo, R.; Guengerich, F. P. J. Biol. Chem. 2011, 286, 4632-4642 10.1074/jbc.M110.193409
45. Guengerich, F. P. Biol. Chem. 2002, 383, 1553-1564 10.1515/BC.2002.175
46. Guengerich, F. P. Drug Metab. Rev. 2004, 36, 159-197 10.1081/DMR-120033996
47. Wang, M.; Roberts, D. L.; Paschke, R.; Shea, T. M.; Masters, B. S. S.; Kim, J-J. P. Proc. Natl. Acad. Sci. U. S. A. 1997, 94, 8411-8416 10.1073/pnas.94.16.8411
48. Harris, C. M.; Roberson, J. S.; Harris, T. M. J. Am. Chem. Soc. 1976, 98, 5380-5386 10.1021/ja00433a053
49. The PyMOL Molecular Graphics System, Version 1.3; Schrödinger, LLC, New York, 2010.
50. Legault, C. Y. CYLview, 1.0b; Université de Sherbrooke: Sherbrooke, Quebec, Canada, 2009; available via the Internet at: http://www.cylview.org.