Hyperconjugation with lone pair of morpholine nitrogen stabilizes transition state for phenyl hydroxylation in CYP3A4 metabolism of (S)-N-[1-(3-morpholin-4-yl phenyl) ethyl]-3-phenylacrylamide

Chemical Physics Letters

Volumn 419, Issue 4-6, 2006, Pages 523-527

  Shaikh, Abdul Rajjak ^a   Broclawik, Ewa ^a,b   Ismael, Mohamed ^a   Tsuboi, Hideyuki ^a   Koyama, Michihisa ^a   Kubo, Momoji ^a,c   Del Carpio, Carlos A ^a   Miyamoto, Akira ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b INSTITUTE OF CATALYSIS AND SURFACE CHEMISTRY   (Poland)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYLATION; METABOLISM; NITROGEN; PHASE TRANSITIONS; PHENOLS;

AROMATICITY; QUANTUM CHEMICAL MODELING;

AMINES;

EID: 32344444515     PISSN: 00092614     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cplett.2005.12.015     Document Type: Article

References (14)

1. Y.J. Wu, C.D. Davis, S. Dworetzky, W.C. Fitzpatrick, D. Harden, H. He, R.J. Knox, A.E. Newton, T. Philip, C. Polson, D.V. Sivarao, L. Sun, S. Tertyshnikova, D. Weaver, S. Yeola, M. Zoeckler, and M.W. Sinz J. Med. Chem. 46 2003 3778
2. S.P. de Visser, and S. Shaik J. Am. Chem. Soc. 125 2003 7413
3. S. Shaik, D. Kumar, S.P. de Visser, A. Altun, and W. Thiel Chem. Rev. 105 2005 2279
4. P.A. Williams, J. Cosme, D.M. Vinkovic, A. Ward, H.C. Angove, P.J. Day, C. Vonrhein, I.J. Tickle, and H. Jhoti Science 305 2004 683
5. J.K. Yano, M.R. Wester, G.A. Schoch, K.J. Griffin, C.D. Stout, and E.F. Johnson J. Biol. Chem. 279 2004 38091
6. J.C. Schoneboom, F. Neese, and W. Thiel J. Am. Chem. Soc. 127 2005 5840
7. M.D. Paulsen, and R.L. Ornstein Proteins 11 1991 184 We thank Prof. G.D. Szklarz and Mr. S. Ericksen, Department of Basic Pharmaceutical Sciences, West Virginia University for kindly providing CVFF parameters for heme
8. T. Kamachi, and K. Yoshizawa J. Am. Chem. Soc. 125 2003 4652
9. B. Delley J. Chem. Phys. 92 1990 508
10. B. Delley J. Chem. Phys. 113 2000 7756
11. R. Raharintsalama, H. Munakata, M. Koyama, M. Kubo, and A. Miyamoto Appl. Surf. Sci. 244 2005 631
12. Accelrys Inc., Materials Studio Getting Started, Accelrys Inc., San Diego, 2002.
13. C.M. Bathelt, L. Ridder, A.J. Mulholland, and J.N. Harvey Org. Biomol. Chem. 2 2004 2998
14. C.M. Bathelt, L. Ridder, A.J. Mulholland, and J.N. Harvey J. Am. Chem. Soc. 125 2003 15004