Prochiral sulfide probes for the active-site topography of rabbit flavin-containing monooxygenase 2 (FMO2)

Tetrahedron Asymmetry

Volumn 8, Issue 4, 1997, Pages 613-618

  Fisher, Michael B ^a   Rettie, Allan E ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SULFIDE; UNSPECIFIC MONOOXYGENASE;

ARTICLE; ENZYME LOCALIZATION; ENZYME SPECIFICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LUNG; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; RABBIT; STEREOCHEMISTRY;

EID: 0031579446     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00033-5     Document Type: Article

References (29)

1. 1. (a) Ziegler, D. M. Annu. Rev. Pharmacol. Toxicol. 1993, 33, 179-199.
2. (b) Ziegler, D. M. TiPS 1990, 11, 321-324.
3. (c) Ziegler, D. M. Microsomal flavin-containing monooxygenase: oxygenation of nucleophilic nitrogen and sulfur compounds, in Enzymatic Basis of Detoxication, Jakoby, W. B., Ed., Vol.1, Academic Press, New York, 1980, 201-227.
4. 2. (a) Villaverde, C.; Alvarez, A. I.; Redondo, P.; Voces, J.; Del Estal, J. L.; Prieto, J. G. Xenobiotica 1995, 25, 433-441.
5. (b) Cashman, J. R.; Park, S. B.; Yang, Z.; Washington, C. B.; Gomez, D. Y.; Giacomini, K. M.; Brett, C. M. Drug Metab. Dispos. 1993, 21, 587-597.
6. (c) Cashman, J. R. Chem. Res. Toxicol. 1995, 8, 165-181.
7. (d) Cashman, J. R. Mol. Pharmacol. 1989, 36, 497-503.
8. 3. (a) Lomri, N.; Yang, Z.; Cashman, J. R. Chem. Res. Toxicol. 1993, 6, 800-807.
9. (b) Nagata, T.; Williams, D. E.; Ziegler, D. M. Chem. Res. Toxicol. 1990, 3, 372-376.
10. (c) Poulsen, L. L.; Taylor, K.; Williams, D. E.; Masters, B. S. S.; Ziegler, D. M. Mol. Pharmacol. 1986, 30, 680-685.
11. 4. (a) Rettie, A. E.; Bogucki, B. D.; Lim, I.; Meier, G. P. Mol. Pharmacol. 1990, 37, 643-651.
12. (b) Sadeque, A. J. M.; Eddy, A. C.; Meier, G. P.; Rettie, A. E. Drug Metab. Dispos. 1992, 20, 832-839.
13. (c) Rettie, A. E.; Meier, G. P.; Sadeque, A. J. M. Chem.-Biol. Interact. 1995, 96, 3-15.
14. (d) Rettie, A. E.; Lawton, M. P.; Sadeque, A. J. M.; Meier, G. P.; Philpot, R. M. Arch. Biochem. Biophys. 1994, 311, 369-377.
15. 5. (a) Light, D. R.; Waxman, D. J.; Walsh, C. Biochemistry 1982, 21, 2490-2498.
16. (b) Allenmark, S. G.; Andersson, M. A. Tetrahedron: Asymmetry 1996, 7, 1089-1094.
17. (c) Ozaki, S.; Ortiz de Montellano, P. R. J. Am. Chem. Soc. 1995, 117, 7056-7064.
18. (d) Carrea, G.; Redigolo, B.; Riva, S.; Colonna, S.; Gaggero, N.; Battistel, E.; Bianchi, D. Tetrahedron: Asymmetry 1992, 3, 1063-1068.
19. (e) Ottolina, G.; Pasta, P.; Carrea, G.; Colonna, S.; Dallavalle, S.; Holland, H. L. Tetrahedron: Asymmetry 1995, 6, 1375-1386.
20. (f) Ryerson, C. C.; Ballou, D. P.; Walsh, C. Biochemistry 1982, 27, 2644-2655.
21. (g) Fujimori, K.; Matsuura, T.; Mikami, A.; Watanabe, Y.; Oae, S.; Iyanagi, T. J. Chem. Soc. Perkin Trans. 1 1990, 1435-1440.
22. (h) Auret, B. J.; Boyd, D. R.; Henbest, H. B.; Ross, S. J. Chem. Soc. C 1968, 2371-2374.
23. 6. (a) Bharme, S.; Bhagwat, S. V.; Shankar, S. K.; Williams, D. E.; Ravindranath, V. J. Pharm. Exp. Ther. 1993, 267, 555-559.
24. (b) Bharme, S.; Bhagwat, S. V.; Shankar, S. K.; Boyd, M. R.; Ravindranath, V. Brain Res. 1995, 672, 276-280.
25. 7. (a) Solladié, G.; Hutt, J.; Girardin, A. Synthesis 1987, 173.
26. (b) Mislow, K.; Green, M. M.; Laur, P.; Melillo, J. T.; Simmons, T.; Ternay, A. L., Jr. J. Am. Chem. Soc. 1965, 87, 1958-1976.
27. 8. Boyd, D. R.; Walsh, C. T.; Chen; Y.-C. J., S-Oxygenases, II: Chirality of Sulfoxidation Reactions, in: Sulfur-Containing Drugs and Related Compounds, Damani, L. S. Ed., Vol. 2, Part A, Ellis Horwood, Chichester, England, 1989, 67-100.
28. 9. Fisher, M. B.; Lawton, M. P.; Atta-Asafo-Adjei, E.; Philpot, R. M.; Rettie, A. E. Drug Metab. Dispos. 1995, 23, 1431-1433.
29. 10. Lam, L. K. P.; Hui, R. A. H. F.; Jones, J. B. J. Org. Chem. 1986, 57, 2047-2050.