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Volumn 22, Issue 13, 2016, Pages 4408-4412

Direct Observation of an Oxepin from a Bacterial Cytochrome P450-Catalyzed Oxidation

(8) Stok, Jeanette E a Chow, Sharon a Krenske, Elizabeth H a Farfan Soto, Clementina a Matyas, Csongor b Poirier, Raymond A b Williams, Craig M a De Voss, James J a

a UNIVERSITY OF QUEENSLAND (Australia)

b MEMORIAL UNIVERSITY OF NEWFOUNDLAND (Canada)

Author keywords

arene oxide; benzene oxide; cytochrome p450; oxepin; tert butyl benzene

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; ATOMS; BENZENE; BIOCHEMISTRY; BIODEGRADATION; CATALYSIS; HYDROXYLATION;

ALIPHATIC HYDROXYLATION; ARENE OXIDES; AROMATIC HYDROXYLATION; C-H FUNCTIONALIZATION; CYTOCHROME P450; DIRECT OBSERVATIONS; HYDROGEN ATOM ABSTRACTION; OXEPIN;

OXIDATION;

CYTOCHROME P450; OXEPINE DERIVATIVE; OXIDE;

CATALYSIS; CHEMISTRY; HYDROXYLATION; METABOLISM; OXIDATION REDUCTION REACTION;

CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; HYDROXYLATION; OXEPINS; OXIDATION-REDUCTION; OXIDES;

EID: 84960803127 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201600246 Document Type: Article

Times cited : (25)

References (48)

1
- 73249132581
- D. Nelson, Human Genomics 2009, 4, 59;
- (2009) Human Genomics , vol.4 , pp. 59
- Nelson, D.¹

2
- 84892193594
- 3 rd ed. (Ed.: P. R. Ortiz de Montellano), Kluwer Academic/Plenum Publishers, New York
- P. R. Ortiz de Montellano, J. J. De Voss, in Cytochrome P450: Structure, Mechanism, and Biochemistry 3 rd ed., (Ed.: P. R. Ortiz de Montellano,), Kluwer Academic/Plenum Publishers, New York, 2005, pp. 183-245.
- (2005) Cytochrome P450: Structure, Mechanism, and Biochemistry , pp. 183-245
- Ortiz De Montellano, P.R.¹ De Voss, J.J.²

3
- 33645460847
- 3 rd ed. (Ed.: P. R. Ortiz de Montellano), Kluwer Academic/Plenum Publishers, New York
- Cytochrome P450: Structure, Mechanism, and Biochemistry, 3 rd ed., (Ed.: P. R. Ortiz de Montellano,), Kluwer Academic/Plenum Publishers, New York, 2005;
- (2005) Cytochrome P450: Structure, Mechanism, and Biochemistry

4
- 79951562057
- P. R. Ortiz de Montellano, S. D. Nelson, Arch. Biochem. Biophys. 2011, 507, 95-110.
- (2011) Arch. Biochem. Biophys. , vol.507 , pp. 95-110
- Ortiz De Montellano, P.R.¹ Nelson, S.D.²

5
- 78149373621
- J. Rittle, M. T. Green, Science 2010, 330, 933-937;
- (2010) Science , vol.330 , pp. 933-937
- Rittle, J.¹ Green, M.T.²

6
- 84887761225
- T. H. Yosca, J. Rittle, C. M. Krest, E. L. Onderko, A. Silakov, J. C. Calixto, R. K. Behan, M. T. Green, Science 2013, 342, 825-829.
- (2013) Science , vol.342 , pp. 825-829
- Yosca, T.H.¹ Rittle, J.² Krest, C.M.³ Onderko, E.L.⁴ Silakov, A.⁵ Calixto, J.C.⁶ Behan, R.K.⁷ Green, M.T.⁸

7
- 33845789243
- M. J. Cryle, J. J. De Voss, Angew. Chem. Int. Ed. 2006, 45, 8221-8223;
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 8221-8223
- Cryle, M.J.¹ De Voss, J.J.²

8
- 34250831288
- Angew. Chem. 2006, 118, 8401-8403;
- (2006) Angew. Chem. , vol.118 , pp. 8401-8403

9
- 84879073481
- B. Wang, C. Li, K.-B. Cho, W. Nam, S. Shaik, J. Chem. Theory Comput. 2013, 9, 2519-2525;
- (2013) J. Chem. Theory Comput. , vol.9 , pp. 2519-2525
- Wang, B.¹ Li, C.² Cho, K.-B.³ Nam, W.⁴ Shaik, S.⁵

10
- 22344450283
- T. Nomura, T. Kushiro, T. Yokota, Y. Kamiya, G. J. Bishop, S. Yamaguchi, J. Biol. Chem. 2005, 280, 17873-17879;
- (2005) J. Biol. Chem. , vol.280 , pp. 17873-17879
- Nomura, T.¹ Kushiro, T.² Yokota, T.³ Kamiya, Y.⁴ Bishop, G.J.⁵ Yamaguchi, S.⁶

11
- 27744585828
- T.-W. Kim, J.-Y. Hwang, Y.-S. Kim, S.-H. Joo, S. C. Chang, J. S. Lee, S. Takatsuto, S.-K. Kim, Plant Cell 2005, 17, 2397-2412.
- (2005) Plant Cell , vol.17 , pp. 2397-2412
- Kim, T.-W.¹ Hwang, J.-Y.² Kim, Y.-S.³ Joo, S.-H.⁴ Chang, S.C.⁵ Lee, J.S.⁶ Takatsuto, S.⁷ Kim, S.-K.⁸

12
- 84899936828
- A. B. McQuarters, M. W. Wolf, A. P. Hunt, N. Lehnert, Angew. Chem. Int. Ed. 2014, 53, 4750-4752;
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 4750-4752
- McQuarters, A.B.¹ Wolf, M.W.² Hunt, A.P.³ Lehnert, N.⁴

13
- 84954272114
- Angew. Chem. 2014, 126, 4846-4848.
- (2014) Angew. Chem. , vol.126 , pp. 4846-4848

14
- 0016228330
- D. M. Jerina, J. W. Daly, Science 1974, 185, 573-582.
- (1974) Science , vol.185 , pp. 573-582
- Jerina, D.M.¹ Daly, J.W.²

15
- 0035996330
- Q. Chen, J. S. Ngui, G. A. Doss, R. W. Wang, X. Cai, F. P. DiNinno, T. A. Blizzard, M. L. Hammond, R. A. Stearns, D. C. Evans, T. A. Baillie, W. Tang, Chem. Res. Toxicol. 2002, 15, 907-914;
- (2002) Chem. Res. Toxicol. , vol.15 , pp. 907-914
- Chen, Q.¹ Ngui, J.S.² Doss, G.A.³ Wang, R.W.⁴ Cai, X.⁵ DiNinno, F.P.⁶ Blizzard, T.A.⁷ Hammond, M.L.⁸ Stearns, R.A.⁹ Evans, D.C.¹⁰ Baillie, T.A.¹¹ Tang, W.¹²

16
- 34047243800
- T. Shimada, Drug Metab. Pharmacokinet. 2006, 21, 257-276;
- (2006) Drug Metab. Pharmacokinet. , vol.21 , pp. 257-276
- Shimada, T.¹

17
- 27544482086
- P. M. Dansette, G. Bertho, D. Mansuy, Biochem. Biophys. Res. Commun. 2005, 338, 450-455;
- (2005) Biochem. Biophys. Res. Commun. , vol.338 , pp. 450-455
- Dansette, P.M.¹ Bertho, G.² Mansuy, D.³

18
- 0031194562
- A. M. Hissink, M. J. Oudshoorn, B. V. Ommen, P. J. V. Bladeren, Toxicol. Appl. Pharmacol. 1997, 145, 1-9.
- (1997) Toxicol. Appl. Pharmacol. , vol.145 , pp. 1-9
- Hissink, A.M.¹ Oudshoorn, M.J.² Ommen, B.V.³ Bladeren, P.J.V.⁴

19
- 79957951707
- C. J. C. Whitehouse, N. H. Rees, S. G. Bell, L.-L. Wong, Chem. Eur. J. 2011, 17, 6862-6868.
- (2011) Chem. Eur. J. , vol.17 , pp. 6862-6868
- Whitehouse, C.J.C.¹ Rees, N.H.² Bell, S.G.³ Wong, L.-L.⁴

20
- 4544344684
- D. J. Edwards, W. H. Gerwick, J. Am. Chem. Soc. 2004, 126, 11432-11433;
- (2004) J. Am. Chem. Soc. , vol.126 , pp. 11432-11433
- Edwards, D.J.¹ Gerwick, W.H.²

21
- 76049121881
- M. U. Huynh, M. C. Elston, N. M. Hernandez, D. B. Ball, S.-i. Kajiyama, K. Irie, W. H. Gerwick, D. J. Edwards, J. Nat. Prod. 2010, 73, 71-74.
- (2010) J. Nat. Prod. , vol.73 , pp. 71-74
- Huynh, M.U.¹ Elston, M.C.² Hernandez, N.M.³ Ball, D.B.⁴ Kajiyama S.-i.⁵ Irie, K.⁶ Gerwick, W.H.⁷ Edwards, D.J.⁸

22
- 0000772808
- D. Jerina, J. Daly, B. Witkop, P. Zaltzman-Nirenberg, S. Udenfriend, Arch. Biochem. Biophys. 1968, 128, 176-183.
- (1968) Arch. Biochem. Biophys. , vol.128 , pp. 176-183
- Jerina, D.¹ Daly, J.² Witkop, B.³ Zaltzman-Nirenberg, P.⁴ Udenfriend, S.⁵

23
- 0031409114
- A. B. Lindstrom, K. Yeowell-O'Connell, S. Waidyanatha, B. T. Golding, R. Tornero-Velez, S. M. Rappaport, Carcinogenesis 1997, 18, 1637-1641;
- (1997) Carcinogenesis , vol.18 , pp. 1637-1641
- Lindstrom, A.B.¹ Yeowell-O'Connell, K.² Waidyanatha, S.³ Golding, B.T.⁴ Tornero-Velez, R.⁵ Rappaport, S.M.⁶

24
- 0031408978
- M. R. Lovern, M. J. Turner, M. Meyer, G. L. Kedderis, W. E. Bechtold, P. M. Schlosser, Carcinogenesis 1997, 18, 1695-1700;
- (1997) Carcinogenesis , vol.18 , pp. 1695-1700
- Lovern, M.R.¹ Turner, M.J.² Meyer, M.³ Kedderis, G.L.⁴ Bechtold, W.E.⁵ Schlosser, P.M.⁶

25
- 0016591915
- H. Selander, D. Jerina, J. Daly, Arch. Biochem. Biophys. 1975, 168, 309-321;
- (1975) Arch. Biochem. Biophys. , vol.168 , pp. 309-321
- Selander, H.¹ Jerina, D.² Daly, J.³

26
- 0016860266
- H. G. Selander, D. M. Jerina, D. E. Piccolo, G. A. Berchtold, J. Am. Chem. Soc. 1975, 97, 4428-4430.
- (1975) J. Am. Chem. Soc. , vol.97 , pp. 4428-4430
- Selander, H.G.¹ Jerina, D.M.² Piccolo, D.E.³ Berchtold, G.A.⁴

27
- 0024465250
- K. R. Korzekwa, D. C. Swinney, W. F. Trager, Biochemistry 1989, 28, 9019-9027.
- (1989) Biochemistry , vol.28 , pp. 9019-9027
- Korzekwa, K.R.¹ Swinney, D.C.² Trager, W.F.³

28
- 0027216023
- I. M. C. M. Rietjens, A. E. M. F. Soffers, C. Veeger, J. Vervoort, Biochemistry 1993, 32, 4801-4812.
- (1993) Biochemistry , vol.32 , pp. 4801-4812
- Rietjens, I.M.C.M.¹ Soffers, A.E.M.F.² Veeger, C.³ Vervoort, J.⁴

29
- 0038110968
- S. P. de Visser, S. Shaik, J. Am. Chem. Soc. 2003, 125, 7413-7424;
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 7413-7424
- De Visser, S.P.¹ Shaik, S.²

30
- 0021766923
- R. P. Hanzlik, K. Hogberg, C. M. Judson, Biochemistry 1984, 23, 3048-3055;
- (1984) Biochemistry , vol.23 , pp. 3048-3055
- Hanzlik, R.P.¹ Hogberg, K.² Judson, C.M.³

31
- 0344236096
- C. M. Bathelt, L. Ridder, A. J. Mulholland, J. N. Harvey, J. Am. Chem. Soc. 2003, 125, 15004-15005;
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 15004-15005
- Bathelt, C.M.¹ Ridder, L.² Mulholland, A.J.³ Harvey, J.N.⁴

32
- 8344222648
- C. M. Bathelt, L. Ridder, A. J. Mulholland, J. N. Harvey, Org. Biomol. Chem. 2004, 2, 2998-3005;
- (2004) Org. Biomol. Chem. , vol.2 , pp. 2998-3005
- Bathelt, C.M.¹ Ridder, L.² Mulholland, A.J.³ Harvey, J.N.⁴

33
- 77349115125
- S. Shaik, S. Cohen, Y. Wang, H. Chen, D. Kumar, W. Thiel, Chem. Rev. 2010, 110, 949-1017.
- (2010) Chem. Rev. , vol.110 , pp. 949-1017
- Shaik, S.¹ Cohen, S.² Wang, Y.³ Chen, H.⁴ Kumar, D.⁵ Thiel, W.⁶

34
- 79951496619
- S. Shaik, P. Milko, P. Schyman, D. Usharani, H. Chen, J. Chem. Theory Comput. 2011, 7, 327-339.
- (2011) J. Chem. Theory Comput. , vol.7 , pp. 327-339
- Shaik, S.¹ Milko, P.² Schyman, P.³ Usharani, D.⁴ Chen, H.⁵

35
- 84981766367
- E. Vogel, H. Günther, Angew. Chem. Int. Ed. Engl. 1967, 6, 385-401;
- (1967) Angew. Chem. Int. Ed. Engl. , vol.6 , pp. 385-401
- Vogel, E.¹ Günther, H.²

36
- 0008945018
- Angew. Chem. 1967, 79, 429-446;
- (1967) Angew. Chem. , vol.79 , pp. 429-446

37
- 84455189162
- H. Jansen, J. C. Slootweg, K. Lammertsma, Beilstein J. Org. Chem. 2011, 7, 1713-1721.
- (2011) Beilstein J. Org. Chem. , vol.7 , pp. 1713-1721
- Jansen, H.¹ Slootweg, J.C.² Lammertsma, K.³

38
- 0032523238
- O. Sibbesen, Z. P. Zhang, P. R. Ortiz de Montellano, Arch. Biochem. Biophys. 1998, 353, 285-296.
- (1998) Arch. Biochem. Biophys. , vol.353 , pp. 285-296
- Sibbesen, O.¹ Zhang, Z.P.² Ortiz De Montellano, P.R.³

39
- 0037008778
- D. Hawkes, G. Adams, A. Burlingame, P. Ortiz de Montellano, J. De Voss, J. Biol. Chem. 2002, 277, 27725-27732;
- (2002) J. Biol. Chem. , vol.277 , pp. 27725-27732
- Hawkes, D.¹ Adams, G.² Burlingame, A.³ Ortiz De Montellano, P.⁴ De Voss, J.⁵

40
- 84930216560
- J. E. Stok, K. E. Slessor, A. J. Farlow, D. B. Hawkes, J. J. De Voss, Adv. Exp. Med. Biol. 2015, 851, 319-339.
- (2015) Adv. Exp. Med. Biol. , vol.851 , pp. 319-339
- Stok, J.E.¹ Slessor, K.E.² Farlow, A.J.³ Hawkes, D.B.⁴ De Voss, J.J.⁵

41
- 33947489861
- R. A. Benkeser, M. L. Burrous, J. J. Hazdra, E. M. Kaiser, J. Org. Chem. 1963, 28, 1094-1097.
- (1963) J. Org. Chem. , vol.28 , pp. 1094-1097
- Benkeser, R.A.¹ Burrous, M.L.² Hazdra, J.J.³ Kaiser, E.M.⁴

42
- 0000987950
- E. Vogel, R. Schubart, W. A. Böll, Angew. Chem. Int. Ed. Engl. 1964, 3, 510;
- (1964) Angew. Chem. Int. Ed. Engl. , vol.3 , pp. 510
- Vogel, E.¹ Schubart, R.² Böll, W.A.³

43
- 0040244745
- Angew. Chem. 1964, 76, 784.
- (1964) Angew. Chem. , vol.76 , pp. 784

44
- 84981761223
- W. Hückel, U. Wörffel, Chem. Ber. 1955, 88, 338-345.
- (1955) Chem. Ber. , vol.88 , pp. 338-345
- Hückel, W.¹ Wörffel, U.²

45
- 0013195385
- C. C. Pye, J. D. Xidos, R. A. Poirier, D. J. Burnell, J. Phys. Chem. A 1997, 101, 3371-3376;
- (1997) J. Phys. Chem. A , vol.101 , pp. 3371-3376
- Pye, C.C.¹ Xidos, J.D.² Poirier, R.A.³ Burnell, D.J.⁴

46
- 84889094474
- J. Morgan, A. Greenberg, Struct. Chem. 2013, 24, 1945-1956.
- (2013) Struct. Chem. , vol.24 , pp. 1945-1956
- Morgan, J.¹ Greenberg, A.²

47
- 84928112792
- R.-Z. Liao, P. E. M. Siegbahn, Chem. Sci. 2015, 6, 2754-2764.
- (2015) Chem. Sci. , vol.6 , pp. 2754-2764
- Liao, R.-Z.¹ Siegbahn, P.E.M.²

48
- 84877833008
- C.-J. Guo, H.-H. Yeh, Y.-M. Chiang, J. F. Sanchez, S.-L. Chang, K. S. Bruno, C. C. C. Wang, J. Am. Chem. Soc. 2013, 135, 7205-7213.
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 7205-7213
- Guo, C.-J.¹ Yeh, H.-H.² Chiang, Y.-M.³ Sanchez, J.F.⁴ Chang, S.-L.⁵ Bruno, K.S.⁶ Wang, C.C.C.⁷

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