Abstract
Correlation of the structure of enzymes with their catalytic activity is one of the most fundamental challenges of structural biology. Ultimately, the various features that characterize the action of enzymes may be understood at a molecular level. These include physical factors, i.e. how the substrates are bound, and chemical factors, i.e. the chemical mechanism of the enzymatic reaction. Our concern here is mostly with the first of these points, since all current evidence shows that binding of the substrates to the active site of heme proteins involved in biological oxidations is the main source of chemoselectivity associated with the enzyme catalyzed reactions, including stereoselectivity and enantioselectivity.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
A.R. Fersht: Enzyme Structure and Mechanism, Chapter 12, W.H. Freeman, New York (1985).
D.D. Hackney: Enzymes 19, 1 (1990).
F.M. Menger: Biochemistry 31, 5368 (1992).
D.P. O’Keefe and P.A. Hard: Mof. 91Ticroóiol. 5, 2099 (1991).
I.C. Gunsalus, P.K. Bhattacharya and K. Suhara: Curr. Top. Cell. *gut. 26, 295 (1986).
F.P. Guengerich ed.: Mammalian Cytochromes P-450, CRC Press, Boca Raton, FL (1987).
J.-L. Riviere and F. Cabanne: Biochimie 69, 743 (1987).
S.D. Black and M.J. Coon: Adv. Enzymol. *lat. Areas Mol. Biol. 60, 35 (1987).
T. Andersson and L. Foerlin: Aquas. Toxicof. 24, 1 (1992).
R. Feyereisen, F.A. Carino and J.F. Koener: 9ev. Pectic. Toxicol. 1, 163 (1991).
D.R. Nelson et al.: DNA Cell Biol. 12, 1 (1993).
R.P. Donaldson and D.G. Luster: Plant Physiol. 96, 669 (1991).
F. Durst: Microbial and Plant Cytochrome P450: Biochemical Characteristics, Genetic Engineering and Practical Implications (eds. K. Ruckpaul and A. Rein), p. 191, Akademic Verlag, Berlin (1989).
F.P. Guengerich: FASBB5. 6, 745 (1992).
M.R. Waterman: Curr. Opin. Struct. Biot. 2, 384 (1992).
S.D. Black: FASBB5. 6, 680 (1992).
D.W. Nebert and D.R. Nelson: Methods Enzymot. 206, 3 (1991).
F.P. Guengerich and T.L. Macdonald: FASBB5. 4, 2453 (1990).
T.D. Porter and M.J. Coon: 5. Biot Chem- 266, 13469 (1991).
M.J. Coon, X. Ding, S. J. Pernecky and A.D.N. Vaz: FASBB 5. 6, 669 (1992).
F.P. Guengerich: Crit. 9çv. Biochem. Mot. Biat 25, 97 (1990).
P.R. Ortiz de Montellano:’Trends Pharn aco[. Sci. 10, 354 (1989).
F.P. Guengerich: 5. Blot. Chem. 266, 10019 (1991).
J.B. Schenkman: Molecular Aspects of Monooxygenases and Bioactivation of Toxic Compounds (eds. E. Arinç et al.), p. 1, Plenum Press, New York (1991).
T.L. Poulos, B.C. Finzel, I.C. Gunsalus, G.C. Wagner and J. Kraut: 5. Biot Chem. 260, 16122 (1985).
T.L. Poulos, B.C. Finzel and A. J. Howard: 5. 9v[ot Blot. 195, 687 (1987).
T.L. Poulos, B.C. Finzel and A.J. Howard: Biochemistry 25, 5314
R. Raag and T.L. Poulos: Bioche
R. Raag and T.L. Poulos: Biochemistry
R. Raag and T.L. Poulos: Biochemistry
R. Raag, S.A. Martinis, S.G. S.igar and T.L. Poulos: Biochemistry 30, 11420 (1991).
S.S. Boddupalli, C.A. Haseman, K.G. Ravichandran, J.Y. Lu, J.E. Goldsmith, J. Deisenhofer and J.A. Peterson: Proc. Natl. Acad. Sci. USA 89, 5567 (1992).
R.T. Reuttinger, L.-P. Wen and A.J. Fulco: 5. Blot. Chem. 264, 10987 (1989).
P.S. Stayton and S.G. Sligar: Biochemistry29, 7381 (1990).
P.S. Stayton, T.L. Poulos and S.G. Sugar: Biochemistry 28, 8201 (1989).
W.M. Atkins and S.G. Sligar: 5. Biot Chem. 263, 18842 (1988).
W.M. Atkins and S.G. Sligar: 5. Am. Chem. Soc. 111, 2715 (1989).
C. Di Primo, G. Hui Bon Hoa, P. Douzou and S.G. Sugar: 5. Biot. Chem. 265, 5361 (1990).
M. Imai, H. Shimada, Y. Watanabe, Y. Matsushima-Hibiya, R. Makino, H. Koga, T. Horiuchi and Y. Ishimura: Proc. Wat. Asad Sci. USA 86, 7823 (1989).
S.A. Martinis, W.M. Atkins, P.S. Stayton and S.G. Sugar: 5. Am. Chem. Soc. 111, 9252 (1989).
H. Shimada, Y. Watanabe, M. Imai, R. Makino, H. Koga, T. Horiuchi and Y. Ishimura: Dioxygen Activation and Homogeneous Catalytic Oxidation (ed. L.I. Simandi), p. 313, Elsevier, Amsterdam (1991).
T.L. Poulos and R. Raag: FASEB5. 6, 674 (1992).
N.C. Gerber and S.G. Sligar: 5. Am. Chem. Soc. 114, 8742 (1992).
P.R. Ortiz de Montellano, J.A. Fruetel, J.R. Collins, D.L. Camper and G.H. Loew: 5. Am. Chem. Soc. 113, 3195 (1991).
J.A. Fruetel, J.R. Collins, D.L. Camper, G.H. Loew and P.R. Ortiz de Montellano: 5.54m. Chem. Soc. 114, 6987 (1992).
Y. Watanabe and Y. Ishimura: 5. Am. Chem. Soc. 111, 410 (1989).
B. Filipovic, M.D. Paulsen, P.J. Loida, S.G. Sligar and R.L. Ornstein: Biochem. Biophys. 9s. Commun. 189, 488 (1992).
J.P. Jones, W.F. Trager and T.J. Carlson: 5. Am. Chem. Soc. 115, 381 (1993).
W.M. Atkins and S.G. Sligar: 5. Am. Chem. Soc. 109, 3754 (1987).
M.D. Paulsen and R.L. Ornstein: Abstract 283, 8th International Symposium on Microsomes and Drug Oxidations, Stockholm, Sweden, June 25–29 (1990).
P.A. Cole and C.H. Robinson: 5. Med Chem. 33, 2933 (1990).
T.L. Poulos: Methods Bnzymot 206, 11 (1991).
D.R. Nelson and H.W. Strobel: 5. Bio(. Chem. 263, 6038 (1988).
D.R. Nelson and H.W. Strobel: Biochemistry 28, 656 (1989).
V.E. Tretiakov, K.N. Degtyarenko, V.Y. Uvarov and A.I. Archakov: Arch. Biochem. Biophys. 275, 429 (1989).
M.J.J.M. Zvelebil, C.R. Wolf and M. J.E. Sternberg: Protein Eng. 4, 271 (1991).
C.A. Laughton, S. Neidle, M.J.J.M. Zvelebil and M.J.E. Sternberg: Biochem. Biophys. Xçs. Commun. 171, 1160 (1990).
D.F.V. Lewis and H. Moereels: 5. Comput.-Aided Mo(. Design 6, 235 (1992).
C.A. Ouzounis and W.T. Melvin: Eur. 5. Biochem. 198, 307 (1991).
O. Gotoh: 5. Biol. Chem. 267, 83 (1992).
E.F. Johnson: Trends Pharmaco(. Sci. 13, 122 (1992).
E.F. Johnson, T. Kronbach and M.-H. Hsu: FASEB5. 6, 700 (1992).
T. Omura and A. Ito: Methods Enzymot 206, 75 (1991).
T. Kronbach, B. Kemper and E.F. Johnson: Biochemistry 30, 6097 (1991).
K.M. Kedzie et al.: 5. Biot. Chem. 266, 22515 (1991).
Y.-A. He, C.A. Balfour, K.M. K.dzie and J.R. Halpert: Biochemistry 31, 9220 (1992).
R.O. Juvonen, M. Iwasaki and M. Negishi: 5. Biol. Chem. 266, 16431 (1991).
R.L.P. Lindberg and M. Negishi: Nature (London)339, 632 (1989).
R. Lindberg, B. Burkhart, T. Ichikawa and M. Negishi: 5. Biot Chem. 264, 6465 (1989).
M. Ishigooka, T. Shimizu, K. Hiroya and M. Hatano: Biochemistry 31, 1528 (1992).
T. Shimizu, A.J.M. Sadeque, G.N. Sadeque, M. Hatano and Y. FujiiKuriyama: Biochemistry 30, 1490 (1991).
T. Shimizu, O. Ito, M. Hatano and Y. Fujii-Kuriyama: Biochemistry 30, 4659 (1991).
A.G. Krainev, T. Shimizu, M. Ishigooka, K. Hiroya, M. Hatano and Y. Fujii-Kuriyama: Biochemistry 30, 11206 (1991).
M. Delaforge, P. Battioni, J.P. Mahy and D. Mansuy: Chem. -Biot. Interact. 60, 101 (1986).
D. Ringe, G.A. Petsko, D.E. Kerr and P. R. Ortiz de Montellano: Biochemistry 23, 2 (1984).
P. Raag, B.A. Swanson, T.L. Poulos and P.R. Ortiz de Montellano: Biochemistry 29, 8119 (1990).
B.A. Swanson and P.R. Ortiz de Montellano: 5. Am. Chem. Soc. 113, 8146 (1991).
B.A. Swanson, D.R. Dutton, J.M. Lunatta, C.S. Yang and P.R. Ortiz de Montellano: 5. Biot. Chem. 266, 19258 (1991).
B.A. Swanson, J.R. Halpert, L.M. Bornheim and P.R. Ortiz de Montellano: Arch. Biochem. Biophys. 292, 42 (1992).
S.F. Tuck, J.A. Peterson and P.R. Ortiz de Montellano: 5. Biot. Chem. 267, 5614 (1992).
P.R. Ortiz de Montellano, W.K. Chan, S.F. Tuck, R.M. Kaikaus, N.M. Bass and J.A. Peterson: FASBB5. 6, 695 (1992).
S.F. Tuck, S. Graham-Lorence, J.A. Peterson and P.R. Ortiz de Montellano: 5. Biot. Chem. 268, 269 (1993).
S.F. Tuck and P.R. Ortiz de Montellano: Biochemistry 31, 6911 (1992).
M. Murray and F. Reidy: Pharmacof. Xgv. 42, 85 (1990).
L. E. Vickery: Methods Enzymot. 206, 548 (1991).
D.V. Parke, C. Ioannides and D.F.V. Lewis: Can. 5. Physiof. Pharmacof. 69, 537 (1991).
a) L. Koymans et al.: Chem. *s. Toxicot. 5, 211 (1992). (b) D.A. Smith and B.C. Jones: Biochem. Pharmacot 44, 2089 (1992).
L. Castro-Maderal and P.D. Sullivan: EBBS Lett. 296, 249 (1992).
D.R. Boyd, C.T. Walsh and Y.C.J. Chen: Sulfur Containing Drugs and Related Compounds (ed. L.A. Damani), p. 67, Ellis Horwood Ltd., Chichester, U.K. (1989).
T. Tanaka, M. Yamasaki, K. Fujimori, Y.H. Kim and S. Oae: Bull. Chem. Soc. Spn. 56, 2300 (1983).
S. Oae, A. Mikami, T. Matsuura, K. Ogawa-Asada, Y. Watanabe, K. Fujimori and T. Iyanagi: Biochen. Biophys. *s. Commun. 131, 567 (1985).
G. Modena and L. Maioli: azz. Chini. Ital. 87, 1306 (1957).
K. Fujimori, T. Matsuura, A. Mikami, Y. Watanabe and S. Oae: 5. Chem. Soc. Perlin I’Trans., 1435 (1990).
J.R. Cashman, L.D. Olsen and L. Borheim: Chem. cs. Toxicot 3, 344 (1990).
J.R. Cashman, L.D. Olsen and L.M. Borheim: 5. 91m. Chem. Soc. 112, 3191 (1990).
J.R. Cashman and L.D. Olsen: Mo! Pharmacy!. 38, 573 (1991).
J.R. Cashman, L.D. Olsen, D.R. Boyd, R. Austin, S. McMordie, R. Dunlop, and H. Dalton: 5. dim. Chem. Soc. 114, 8772 (1992).
J.C. Alvarez and P.R. Ortiz de Montellano: Biochemistry 31, 8315 (1992).
P.R. Ortiz de Montellano: Cytochrome P-450: Structure, Mechanism, and Biochemistry (ed. P.R. Ortiz de Montellano), p. 217, Plenum Press, New York (1986).
M.J. Gunter and P. Turner: Coord. Chem. 14v. 108, 115 (1991).
D. Ostovic and T.C. Bruice:. Bruice: Acc. Chem. 14.5. 25, 314 (1992).
D. Wistuba, H.P. Nowotny, O. Träger and V. Schurig: Chiratity 1, 127 (1989).
S.K. Yang: Biochem. Pharmacot. 37, 61 (1988).
S.K. Yang, M. Mushtaq, H.B. Weems, D.W. Miller and P.P. Fu: Biochem. 9. 245, 191 (1987).
G.K.B. Prasad and D.R. Thakker: Biochem. Biophys. Jas. Commun. 181, 1516 (1991).
J.H. Capdevila, J.R. Falck and R.W. Estabrook: MEW 5. 6, 731 (1992).
J.H. Capdevila, A. Karara, D.J. Waxman, M.V. Martin, J.R. Falck and F.P.Guengerich: 5. Bid. Chem. 265, 10865 (1990).
F.A. Fitzpatrick and R.C. Murphy: Pharmacot. Rçv. 40, 229 (1989).
A. Karara, E. Dishman, H. Jacobson, J.R. Falck and J.H. Capdevila: 5PBS Lett. 268, 227 (1990).
R.M. Laethem, C.L. Laethem and D.R. Koop: 5. Biot. Chem. 267, 5552 (1992).
H. Tyson: ‘Aeon. pp(. Genet. 84, 643 (1992).
K.G. Welinder: Curr. Opin. Struct. Biot. 2, 388 (1992).
J. Lobarzewski, H. Greppin, C. Penel and T. Gaspar (eds.): Biochemical, Molecular and Physiological Aspects of Plant Peroxidases, University of Geneva, Geneva (1991).
J. Everse, K.E. Everse and M.B. Grisham: Peroxidases in Chemistry and Biology, CRC Press, Boca Raton (1991).
M. Stiborova, E. Frei, H.H. Schmeister and P. Anzenbacher: Drug Meta6. Drug Interact. 9, 177 (1991).
P.F. Hollenberg: FASEB 5. 6, 686 (1992).
H.B. Dunford: See ref. 114, Vol. 2, p. 1.
B.C. Finzel, T.L. Poulos and J. Kraut: 5. Biot. Chem. 259, 13027 (1984).
H.R. Bosshard, H. Anni and T. Yonetani: See ref. 114, Vol. 2, p. 51.
J.H. Dawson: Science 240, 433 (1988).
T.L. Poulos: Adv. Inorg. Biocheni. 7, 1 (1988).
H. Anni and T. Yonetani: stet. Ions Biot. Syst. 28, 219 (1992).
P.R. Ortiz de Montellano: Annu. Rev. Pharmacot Taxicof. 32, 89 (1992).
S.L. Edwards, H.X. Xuong, R.C. Hamlin and J. Kraut: Biochemistry 26, 1503 (1987).
M. Sivaraja, D.B. Goodin, A.G. Mauk, M. Smith and B.A. Hoffman: Science 245, 738 (1989).
L.B. Vitello, J.E. Erman, J.M. Mauro and J. Kraut: Biochim. Biophys. Acta 1038, 90 (1990).
D.K. Bhattacharyya, IJ. Bandyopadhyay and R.K. Banerjee: 5. Biot Chem. 267, 9800 (1992).
L.J. Marnett: Biological Oxidation Systems, Vol. 2, p. 637, Academic Press, New York (1990).
Y. Morita, B. Mikami, H. Yamashita, J.Y. Lee, S. Aibara, M. Sato, Y. Katsube and N. Tanaka: See ref. 113, p. 81.
S.L. Edwards, R. Raag, H. Wariishi, M.H. Gold and T.L. Poulos: Proc. watt. Acad. Sci. USA 90, 750 (1993).
J. Zeng and R.E. Fenna: 5. Mot. Biot. 226, 185 (1992).
J.D. Satterlee, J.E. Erman, J.M. Mauro and J. Kraut: Biochemistry 29, 8797 (1990).
J.E. Erman, L.B. Vitello, M.A. Miller and J. Kraut: 5. Am. Chem. Soc. 114, 6592 (1992).
I. Fita and M.G. Rossman: 5. Mot. Biot. 185, 21 (1985).
K. Choudhury, M. Sundaramoorthy, J.M. Mauro and T.L. Poulos: 5. Biol. Chem. 267, 25656 (1992).
M.A. Ator and P.R. Ortiz de Montellano: 5. Biot. Chem. 262, 1542 (1987).
G.D. DePillis, H. Wariishi, M.H. Gold and P.R. Ortiz de Montellano: Arch. Biochem. Biophys. 280, 217 (1990).
R.Z. Harris, H. Wariishi, M.H. Gold and P.R. Ortiz de Montellano: 5. Biot. Chem. 266, 8751 (1991).
G. DePillis and P.R. Ortiz de Montellano: Biochemistry 28, 7947 (1989).
I. Morishima and S. Ogawa: 5. Biol. Chem. 254, 2814 (1979).
J. Sakurada, S. Takahashi and T. Hosoya: 5. Biot. Chem. 261, 9657 (1986).
S. Modi, D.V. Behere and S. Mitra: Biochim. Biophys. Acta 996, 214 (1989).
L. Casella, M. Gullotti, S. Poli, M. Bonfà , R.P. Ferrari and A. Marchesini: Biochem. 5. 279, 245 (1991).
N.C. Veitch and R.J.P. Williams: Ear. 5. Biochem. 189, 351 (1990).
N.C. Veitch and R.J.P. Williams: See ref. 113, p. 99.
G.N. LaMar, G. Hernanà ndez and J.S. de Ropp: Biochemistry 31, 9158 (1992).
L. Banci, I. Bertini,T. Bini, M. Tien and P. Turano: Submitted for publication.
A.T. Smith, S.A. Sanders, R.N.F. Thorneley, J.F. Burke and R.C. Bray: Bur. 5. Biochem. 207, 507 (1992).
N.C. Veitch, R.J.P. Williams, R.C. Bray, J.F. Burke, S.A. Sanders, R.N.F. Thorneley and A.T. Smith: Bur. 5. Biochem. 207, 521 (1992).
A. Corin, G. McLendon, Q. Zhang, R. Hake, J. Falvo, K. Lu, R. Ciccarelli and D. Holzschu: Biochemistry 30, 11585 (1991).
H. Pelletier and J. Kraut: Science 258, 1748 (1992).
R. Hake, G. McLendon, A. Corin and D. Holzschu: 5. in. Chem. Soc. 114, 5442 (1992).
G.D. DePillis, B.P. Sishta, A.G. Mauk and P.R. Ortiz de Montellano: 5. Bio(. Chem. 266, 19334 (1991).
V.P. Miller, G.D. DePillis, J.C. Ferrer, A.G. Mauk and P.R. Ortiz de Montellano: 5. Biot. Chem. 267, 8936 (1992).
L. Casella, M. Gullotti, S. Poli and E. Santelli: To be submitted for publication.
E.L. Thomas, P.M. Bozeman and D.B. Learn: See ref. 114, Vol. 1, p. 123.
G.S. Bayse, A.W. Michaels and M. Morrison: Biochim. Biophys.Acta 284, 34 (1972).
S. Colonna, N. Gaggero, G. Carrea and P. Pasta: 5. Chem. Soc. Chem. Commun., 357 (1992).
R. Z. Harris, S.L. Newmyer and P.R. Ortiz de Montellano: 5. Biot. Chem. 268, 1637 (1993).
E. Blée and F. Schuber: Biochemistry 28, 4962 (1989).
W.L. Smith, T.E. Eling, R.J. Kulmacz, L. J. Marnett and A. Tsai: Biochemistry 31, 3 (1992).
P. Plé and L.J. Marnett: 5. Bid. Chem. 264, 13983 (1989).
L. Casella, M. Gullotti, R. Ghezzi, S. Poli, T. Beringhelli, S. Colonna and G. Carrea: Biochemistry 31, 9451 (1992).
U. Pérez and H.B. Dunford: Biochim. Biophys. eta 1038, 98 (1990).
U. Pérez and H.B. Dunford: Biochemistry 29, 2757 (1990).
P.R. Ortiz de Montellano, Y.S. Choe, G. DePillis and C.E. Catalano: 5. Biot. Chem. 262, 11641 (1987).
A.A. Elfarra, R.J. Duescher and C.M. Pasch: Arch. Biochem. Biophys. 286, 244 (1991).
D.R. Doerge, N.M. Cooray and M. E. Brewster: Biochemistry 30, 8960 (1991).
S. Kobayashi, M. Nakano, T. Goto, T. Kimura and A.P. Schaap: Biochim. Biophys. 94s. Commun. 135, 166 (1986).
R.J. Duescher and A.A. Elfarra: 9. Biot. Chem. 267, 19859 (1992).
W.D. Hewson and L.P. Hager: The Porphyrins (ed. D. Dolphin), Vol. VII, Part B, p. 295, Academic Press, New York (1979).
B.W. Griffin: See ref. 114, Vol. 2, p. 85.
S.R. Blanke and L.P. Hager: J. Biot. Chem. 263, 18739 (1988).
S.R. Blanke and L.P. Hager: 5. Biot. Chem. 265, 12454 (1990).
L.B. Dugad, X. Wang, C.-C. Wang, G.S. Lukat and H.M. Goff: Biochemistry 31, 1651 (1992).
V.M. Samokyszyn and P.R. Ortiz de Montellano: Biochemistry 30, 11646 (1991).
L. Casella, M. Gullotti, C. Selvaggini, S. Poli and T. Beringhelli: Submitted for publication.
D.R. Doerge and M.D. Corbett: Chen rs. Toxrcol. 4, 556 (1991).
A.-M. Lambeir, H.B. Dunford and M.A. Pickard: Bur. 9. Biochem. 163, 123 (1987).
S. Colonna, N. Gaggero, A. Manfredi, L. Casella, M. Gullotti, G. Carrea and P. Pasta: Biochemistry 29, 10466 (1990).
S. Colonna, N. Gaggero, L. Casella, G. Carrea and P. Pasta: Tetrahedron,Asymmetry 3, 95 (1992).
H. Fu, H. Kondo, Y. Ichikawa, G.C. Cook and C.H. Wong: y. Org. Chem. 57, 7265 (1992).
M.B. McCarthy and R.E. White: 9. Bio! Chem. 258, 9153 (1983).
J. Geigert, T.D. Lee, D.J. Dalietos, D.S. Hirano and S.L. Neidleman: Biochem. Biophys. *s. Commun. 136, 778 (1986).
A.A. Elfarra, R.J. Duescher and C.M. Pasch: Arch. Biochem. Biophys. 286, 244 (1991).
S. Colonna, N. Gaggero, L. Casella, G. Carrea and P. Pasta: Tetrahedron Asymmetry 4, 1325 (1993).
C.-H. Wong: Science 244, 1145 (1989).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1994 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Casella, L., Colonna, S. (1994). Biological Oxidations: Stereochemical Aspects. In: Montanari, F., Casella, L. (eds) Metalloporphyrins Catalyzed Oxidations. Catalysis by Metal Complexes, vol 17. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-2247-6_10
Download citation
DOI: https://doi.org/10.1007/978-94-017-2247-6_10
Publisher Name: Springer, Dordrecht
Print ISBN: 978-90-481-4355-9
Online ISBN: 978-94-017-2247-6
eBook Packages: Springer Book Archive