-
1
-
-
33645849237
-
-
(a) Hersleth, H. P.; Ryde, U.; Rydberg, P.; Gorbitz, C. H.; Andersson, K. K. J. Inorg. Biochem. 2006, 100, 460-76.
-
(2006)
J. Inorg. Biochem
, vol.100
, pp. 460-476
-
-
Hersleth, H.P.1
Ryde, U.2
Rydberg, P.3
Gorbitz, C.H.4
Andersson, K.K.5
-
2
-
-
33748353401
-
-
(b) Behan, R. K.; Hoffart, L. M.; Stone, K. L.; Krebs, C.; Green, M. T. J. Am. Chem. Soc. 2006, 128, 11471-4.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 11471-11474
-
-
Behan, R.K.1
Hoffart, L.M.2
Stone, K.L.3
Krebs, C.4
Green, M.T.5
-
3
-
-
33747151589
-
-
(c) Harvey, J. N.; Bathelt, C. M.; Mulholland, A. J. J. Comput. Chem. 2006, 27, 1352-62.
-
(2006)
J. Comput. Chem
, vol.27
, pp. 1352-1362
-
-
Harvey, J.N.1
Bathelt, C.M.2
Mulholland, A.J.3
-
4
-
-
2942679678
-
-
(d) Green, M. T.; Dawson, J. H.; Gray, H. B. Science 2004, 304, 1653-6.
-
(2004)
Science
, vol.304
, pp. 1653-1656
-
-
Green, M.T.1
Dawson, J.H.2
Gray, H.B.3
-
5
-
-
33846483860
-
-
For recent reviews on the mechanisms of cytochrome P450 oxidations, see: (a) Isin, E. M.; Guengerich, F. P. Biochim. Biophys. Acta 2007, 1770, 314-29.
-
For recent reviews on the mechanisms of cytochrome P450 oxidations, see: (a) Isin, E. M.; Guengerich, F. P. Biochim. Biophys. Acta 2007, 1770, 314-29.
-
-
-
-
6
-
-
4644275807
-
-
(b) Meunier, B.; de Visser, S. P.; Shaik, S. Chem. Rev. 2004, 104, 3947-80.
-
(2004)
Chem. Rev
, vol.104
, pp. 3947-3980
-
-
Meunier, B.1
de Visser, S.P.2
Shaik, S.3
-
7
-
-
1842842895
-
-
(c) Makris, T. M.; Davydov, R.; Denisov, I. G.; Hoffman, B. M.; Sligar, S. G. Drug Metab. Rev. 2002, 34, 691-708.
-
(2002)
Drug Metab. Rev
, vol.34
, pp. 691-708
-
-
Makris, T.M.1
Davydov, R.2
Denisov, I.G.3
Hoffman, B.M.4
Sligar, S.G.5
-
8
-
-
33644947157
-
-
For recent reports on cytochrome P450 catalyzed amine oxidations, see: (d) Cerny, M. A.; Hanzlik, R. P. J. Am. Chem. Soc. 2006, 128, 3346-54.
-
For recent reports on cytochrome P450 catalyzed amine oxidations, see: (d) Cerny, M. A.; Hanzlik, R. P. J. Am. Chem. Soc. 2006, 128, 3346-54.
-
-
-
-
9
-
-
24644510168
-
-
(e) Jurva, U.; Bissel, P.; Isin, E. M.; Igarashi, K.; Kuttab, S.; Castagnoli, N., Jr. J. Am. Chem. Soc. 2005, 127, 12368-77.
-
(2005)
J. Am. Chem. Soc
, vol.127
, pp. 12368-12377
-
-
Jurva, U.1
Bissel, P.2
Isin, E.M.3
Igarashi, K.4
Kuttab, S.5
Castagnoli Jr., N.6
-
10
-
-
0037125528
-
-
(f) Shaffer, C. L.; Harriman, S.; Koen, Y. M.; Hanzlik, R. P. J. Am. Chem. Soc. 2002, 124, 8268-74.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 8268-8274
-
-
Shaffer, C.L.1
Harriman, S.2
Koen, Y.M.3
Hanzlik, R.P.4
-
11
-
-
0011080284
-
-
(a) Griffin, B. W.; Davis, D. K.; Bruno, G. V. Bioorg. Chem. 1981, 10, 342-55.
-
(1981)
Bioorg. Chem
, vol.10
, pp. 342-355
-
-
Griffin, B.W.1
Davis, D.K.2
Bruno, G.V.3
-
12
-
-
0024398202
-
-
(b) Van, der Zee, J.; Duling, D. R.; Mason, R. P.; Eling, T. E. J. Biol. Chem. 1989, 264, 19828-36.
-
(1989)
J. Biol. Chem
, vol.264
, pp. 19828-19836
-
-
Van1
der Zee, J.2
Duling, D.R.3
Mason, R.P.4
Eling, T.E.5
-
13
-
-
0035812406
-
-
(c) Shaffer, C. L.; Morton, M. D.; Hanzlik, R. P. J. Am. Chem. Soc. 2001, 123, 8502-8.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 8502-8508
-
-
Shaffer, C.L.1
Morton, M.D.2
Hanzlik, R.P.3
-
14
-
-
0035900964
-
-
(d) Shaffer, C. L.; Morton, M. D.; Hanzlik, R. P. J. Am. Chem. Soc. 2001, 123, 349-50.
-
(2001)
J. Am. Chem. Soc
, vol.123
, pp. 349-350
-
-
Shaffer, C.L.1
Morton, M.D.2
Hanzlik, R.P.3
-
17
-
-
0002154654
-
-
Everse, J, Everse, K. E, Grisham, M. B, Eds, CRC Press: Boca Raton, FL
-
(a) Dunford, H. B. In Peroxidases in Chemistry and Biology; Everse, J., Everse, K. E., Grisham, M. B., Eds.; CRC Press: Boca Raton, FL, 1991; Vol. 2, pp 1-24.
-
(1991)
Peroxidases in Chemistry and Biology
, vol.2
, pp. 1-24
-
-
Dunford, H.B.1
-
18
-
-
0003514551
-
-
John Wiley & Sons, Inc, New York
-
(b) Dunford, H. B. Heme Peroxidases; John Wiley & Sons, Inc.: New York, 1999.
-
(1999)
Heme Peroxidases
-
-
Dunford, H.B.1
-
20
-
-
0037201488
-
-
(a) Sasaki, J. C.; Fellers, R. S.; Colvin, M. E. Mutat. Res. 2002, 506-507, 79-89.
-
(2002)
Mutat. Res
, vol.506-507
, pp. 79-89
-
-
Sasaki, J.C.1
Fellers, R.S.2
Colvin, M.E.3
-
21
-
-
0029970784
-
-
(b) Guengerich, F. P.; Yun, C. H.; Macdonald, T. L. J. Biol. Chem. 1996, 271, 27321-9.
-
(1996)
J. Biol. Chem
, vol.271
, pp. 27321-27329
-
-
Guengerich, F.P.1
Yun, C.H.2
Macdonald, T.L.3
-
22
-
-
0024974070
-
-
(a) Fidy, J.; Paul, K.-G.; Vanderkooi, J. M. Biochemistry 1989, 28, 7531-41.
-
(1989)
Biochemistry
, vol.28
, pp. 7531-7541
-
-
Fidy, J.1
Paul, K.-G.2
Vanderkooi, J.M.3
-
23
-
-
0022974617
-
-
(b) Sukurada, J.; Takahashi, S.; Hosoya, T. J. Biol. Chem. 1986, 261, 9657-62.
-
(1986)
J. Biol. Chem
, vol.261
, pp. 9657-9662
-
-
Sukurada, J.1
Takahashi, S.2
Hosoya, T.3
-
24
-
-
0030570994
-
-
Sayre, L. M.; Naismith, R. T., II; Bada, M. A.; Li, W.-S.; Klein, M. E.; Tennant, M. D. Biochim. Biophys. Acta 1996, 1296, 250-56.
-
(1996)
Biochim. Biophys. Acta
, vol.1296
, pp. 250-256
-
-
Sayre, L.M.1
Naismith II, R.T.2
Bada, M.A.3
Li, W.-S.4
Klein, M.E.5
Tennant, M.D.6
-
30
-
-
38349086691
-
-
Ph.D. Thesis, Case Western Reserve University, Cleveland, OH
-
Li, W.-S. Ph.D. Thesis, Case Western Reserve University, Cleveland, OH, 1997.
-
(1997)
-
-
Li, W.-S.1
-
31
-
-
0024501672
-
-
(a) Elmarakby, S. A.; Duffel, M. W.; Goswami, A.; Sariaslani, F. S.; Rosazza, J. P. N. J. Med. Chem. 1989, 32, 674-9.
-
(1989)
J. Med. Chem
, vol.32
, pp. 674-679
-
-
Elmarakby, S.A.1
Duffel, M.W.2
Goswami, A.3
Sariaslani, F.S.4
Rosazza, J.P.N.5
-
32
-
-
0023779951
-
-
(b) Goswami, A.; Macdonald, T. L.; Hubbard, C.; Duffel, M. W.; Rosazza, J. P. N. Chem. Res. Toxicol. 1988, 1, 238-42.
-
(1988)
Chem. Res. Toxicol
, vol.1
, pp. 238-242
-
-
Goswami, A.1
Macdonald, T.L.2
Hubbard, C.3
Duffel, M.W.4
Rosazza, J.P.N.5
-
37
-
-
0034694898
-
-
(a) Silva, S. O.; Ximenes, V. F.; Catalani, L. H.; Campa, A. Biochem. Biophys. Res. Commun. 2000, 279, 657-62.
-
(2000)
Biochem. Biophys. Res. Commun
, vol.279
, pp. 657-662
-
-
Silva, S.O.1
Ximenes, V.F.2
Catalani, L.H.3
Campa, A.4
-
38
-
-
0035860288
-
-
(b) Ximenes, V. F.; Catalani, L. H.; Campa, A. Biochem. Biophys. Res. Commun. 2001, 287, 130-4.
-
(2001)
Biochem. Biophys. Res. Commun
, vol.287
, pp. 130-134
-
-
Ximenes, V.F.1
Catalani, L.H.2
Campa, A.3
-
39
-
-
0035866576
-
-
(c) Ximenes, V. F.; Campa, A.; Catalani, L. H. Arch. Biochem. Biophys. 2001, 387, 173-9.
-
(2001)
Arch. Biochem. Biophys
, vol.387
, pp. 173-179
-
-
Ximenes, V.F.1
Campa, A.2
Catalani, L.H.3
-
40
-
-
0031854435
-
-
(a) Skordos, K. W.; Skiles, G. K.; Laycock, J. D.; Lanza, D. L.; Yost, G. S. Chem. Res. Toxicol. 1998, 11, 741-9.
-
(1998)
Chem. Res. Toxicol
, vol.11
, pp. 741-749
-
-
Skordos, K.W.1
Skiles, G.K.2
Laycock, J.D.3
Lanza, D.L.4
Yost, G.S.5
-
42
-
-
33645529481
-
-
See for example: a
-
See for example: (a) Shirasaka, N.; Ohnishi, H.; Sato, K.; Miyamoto, R.; Terashita, T.; Yoshizumi, H. J. Biosci. Bioeng. 2005, 100, 653-6.
-
(2005)
J. Biosci. Bioeng
, vol.100
, pp. 653-656
-
-
Shirasaka, N.1
Ohnishi, H.2
Sato, K.3
Miyamoto, R.4
Terashita, T.5
Yoshizumi, H.6
-
43
-
-
0001430976
-
-
(b) Adam, W.; Lazarus, M.; Hoch, U.; Korb, M. N.; Saha-Moeller, C. R.; Schreier, P. J. Org. Chem. 1998, 63, 6123-7.
-
(1998)
J. Org. Chem
, vol.63
, pp. 6123-6127
-
-
Adam, W.1
Lazarus, M.2
Hoch, U.3
Korb, M.N.4
Saha-Moeller, C.R.5
Schreier, P.6
-
44
-
-
0029176375
-
-
(c) Adam, W.; Hoch, U.; Lazarus, M.; Saha-Moeller, C. R.; Schreier, P. J. Am. Chem. Soc. 1995, 117, 11898-901.
-
(1995)
J. Am. Chem. Soc
, vol.117
, pp. 11898-11901
-
-
Adam, W.1
Hoch, U.2
Lazarus, M.3
Saha-Moeller, C.R.4
Schreier, P.5
-
45
-
-
0014944066
-
-
Yeh, R.; Hemphill, D., Jr.; Sell, H. M. Biochemistry 1970, 9, 4229-32.
-
(1970)
Biochemistry
, vol.9
, pp. 4229-4232
-
-
Yeh, R.1
Hemphill Jr., D.2
Sell, H.M.3
-
47
-
-
38349183319
-
-
19
-
19
-
-
-
-
48
-
-
0015523237
-
-
For one example of kinetic saturation for HRP compound II reduction by p-cresol see: Critchlow, J. E.; Dunford, H. B. J. Biol. Chem. 1972, 247, 3703-13.
-
For one example of kinetic saturation for HRP compound II reduction by p-cresol see: Critchlow, J. E.; Dunford, H. B. J. Biol. Chem. 1972, 247, 3703-13.
-
-
-
-
49
-
-
15244346501
-
-
Krammer, A.; Kirchhoff, P. D.; Jiang, X.; Venkatachalam, C. M.; Waldman, M. J. Mol. Graphics Modell. 2005, 23, 395-407.
-
(2005)
J. Mol. Graphics Modell
, vol.23
, pp. 395-407
-
-
Krammer, A.1
Kirchhoff, P.D.2
Jiang, X.3
Venkatachalam, C.M.4
Waldman, M.5
-
50
-
-
0037161809
-
-
Berglund, G. I.; Carlsson, G. H.; Smith, A. T.; Szoke, H.; Henriksen, A.; Hajdu, J. Nature 2002, 417, 463-8.
-
(2002)
Nature
, vol.417
, pp. 463-468
-
-
Berglund, G.I.1
Carlsson, G.H.2
Smith, A.T.3
Szoke, H.4
Henriksen, A.5
Hajdu, J.6
-
51
-
-
33644671184
-
-
Hallingback, H. R.; Gabdoulline, R. R.; Wade, R. C. Biochemistry 2006, 45, 2940-50.
-
(2006)
Biochemistry
, vol.45
, pp. 2940-2950
-
-
Hallingback, H.R.1
Gabdoulline, R.R.2
Wade, R.C.3
-
54
-
-
33645456147
-
-
Colosi, L. M.; Huang, Q.; Weber, W. J., Jr. J. Am. Chem. Soc. 2006, 128, 4041-7.
-
(2006)
J. Am. Chem. Soc
, vol.128
, pp. 4041-4047
-
-
Colosi, L.M.1
Huang, Q.2
Weber Jr., W.J.3
-
55
-
-
33845471467
-
-
On the basis of the voltametrically measured redox potentials of 1-4 (Table 1) relative to the higher values of typical 3-alkylindoles (Waltman, R. J.; Diaz, A. F.; Bargon, J. J. Phys. Chem. 1984, 88, 4343-6), it might be predicted that oxidations of all four indoleethylamines would lead strictly to amine oxidation products. However, oxidation outcome also reflects the fact that it is the indole ring that is bound at the heme edge and is thus closest to the HRP oxidants.
-
On the basis of the voltametrically measured redox potentials of 1-4 (Table 1) relative to the higher values of typical 3-alkylindoles (Waltman, R. J.; Diaz, A. F.; Bargon, J. J. Phys. Chem. 1984, 88, 4343-6), it might be predicted that oxidations of all four indoleethylamines would lead strictly to amine oxidation products. However, oxidation outcome also reflects the fact that it is the indole ring that is bound at the heme edge and is thus closest to the HRP oxidants.
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