Structure and stereochemistry of products of hydroxylation of human steroid hormones by a housefly cytochrome P450 (CYP6A1)

Magnetic Resonance in Chemistry

Volumn 44, Issue 4, 2006, Pages 467-474

  Jacobsen, Neil E ^a   Kövér, Katalin E ^b   Murataliev, Marat B ^a   Feyereisen, René ^c,d   Walker, F Ann ^a  

^a The University of Arizona   (United States)

^b UNIVERSITY OF DEBRECEN   (Hungary)

^c UNIVERSITY OF ARIZONA   (United States)

^d INRA Centre de Recherches d'Antibes   (France)

Author keywords

13C; 1H; Broadband adiabatic shaped pulses; HMBC; Hydroxylation; Insect cytochrome P450; NMR; Steroid A ring conformation; Steroids

Indexed keywords

LIPIDS; NUCLEAR MAGNETIC RESONANCE; STEREOSELECTIVITY; STEROID HORMONES;

13C; 1H; BROADBAND ADIABATIC SHAPED PULSE; CYTOCHROMES P450; HETERONUNCLEAR MULTIPLE BOND CORRELATION; INSECT CYTOCHROME P450; MULTIPLE BONDS; RING CONFORMATIONS; SHAPED PULSE; STEROID; STEROID A-RING CONFORMATION;

HYDROXYLATION;

EID: 33645473355     PISSN: 07491581     EISSN: 1097458X     Source Type: Journal    
DOI: 10.1002/mrc.1767     Document Type: Article

References (36)

1. Guengerich FP, Shimada T. Chem. Res. Toxicol. 1991; 4: 391.
2. Andersen JF, Utermohlen JG, Feyereisen R. Biochemistry 1994; 33: 2171.
3. Andersen JF, Walding JK, Evans PH, Bowers WS, Feyereisen R. Chem. Res. Toxicol. 1997; 10: 156.
4. Cerny I, Fajkos J, Pouzar V. Steroids 1996; 61: 58;
5. Mahato SB, Mukherjee A. J. Steroid Biochem. 1984; 21: 341.
6. Kirk DN, Toms HC, Douglas C, White KA, Smith KE, Latif S, Hubbard RWP. J. Chem. Soc., Perkin Trans. 2 1990; 1567.
7. Kuriyama K, Kondo E, Tori K. Tetrahedron Lett. 1963; 22: 1485.
8. Osawa Y, Gardner JO. J. Org. Chem. 1971; 36: 3246.
9. Mineki S, Iida M, Kato K, Fukaya F, Kita K, Nakamura J, Yoshihama M. J. Ferment. Bioeng. 1995; 80: 223.
10. Bednarski PJ, Nelson SD. J. Med. Chem. 1989; 32: 203;
11. Burnett RD, Kirk DN. J. Chem. Soc., Perkin Trans, 1 1973; 17: 1830.
12. Tweit RC, Kagawa CM. J. Med. Chem. 1964; 53: 524;
13. Kawazoe Y, Sato Y, Okamoto T, Tsuda K. Chem. Pharm. Bull. 1963; 11: 328.
14. Duax WL, Eger C, Pokrywiecki S, Osawa Y. J. Med. Chem. 1971; 14: 295.
15. Bodenhausen G, Ruben DJ. Chem. Phys. Lett. 1980; 69: 185.
16. Summers MF, Marzilli LG, Bax A. J. Am. Chem. Soc. 1986; 108: 4285;
17. Bax A, Marion D. J. Magn. Reson. 1988; 78: 186.
18. Ranee M, Sørensen OW, Bodenhausen G, Wagner G, Ernst RR, Wüthrich K. Biochem. Biophys. Res. Commun. 1983; 117: 479.
19. Jeener J, Meier BH, Bachmann P, Ernst RR. J. Chem. Phys. 1979; 71: 4546;
20. Macura S, Ernst RR. Mol. Phys. 1980; 41: 95.
21. Hurd RE, John BK. J. Magn. Reson. 1991; 91: 648.
22. Willker W, Leibfritz D, Kerssebaum R, Bermel W. Magn. Reson. Chem. 1993; 31: 287.
23. Sheng S, van Halbeek H. J. Magn. Reson. 1998; 130: 296;
24. Cicero DO, Barbato G, Bazzo R. J. Magn. Reson. 2001; 148: 209;
25. Edden RAE, Keeler J. J. Magn. Reson. 2004; 166: 53.
26. Ding K. Magn. Reson. Chem. 2000; 38: 321.
27. Abramovich D, Vega S. J. Magn. Reson., Ser. A 1993; 105: 30.
28. Guzov VM, Houston HL, Murataliev MB, Walker FA, Feyereisen R. J. Biol. Chem. 1996; 271: 26637.
29. Murataliev MB, Arino A, Guzov VM, Feyereisen R. Insect Biochem. Mol. Biol. 1999; 29: 233.
30. Marion D, Wüthrich K. Biochem. Biophys. Res. Commun. 1983; 113: 967.
31. States DJ, Haberkorn RA, Ruben DJ. J. Magn. Reson. 1982; 48: 286.
32. Ancian B, Bourgeois I, Dauphin J-F, Shaw AA. J. Magn. Reson. 1997; 125: 348.
33. Cavanagh J, Palmer AG III, Wright PE, Rance M. J. Magn. Reson. 1991; 91: 429.
34. Wimperis SC, Freeman R. J. Magn. Reson. 1984; 58: 348.
35. Mackin G, Shaka AJ. J. Magn. Reson., Ser. A 1996; 118: 247.
36. Barfield M. Magn. Reson. Chem. 2003; 41: 344.