Cyclization of a cellular dipentaenone by streptomyces coelicolor cytochrome P450 154A1 without oxidation/reduction

Journal of the American Chemical Society

Volumn 132, Issue 43, 2010, Pages 15173-15175

  Cheng, Qian ^a   Lamb, David C ^b   Kelly, Steven L ^b   Lei, Li ^a   Guengerich, F Peter ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b SWANSEA UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL SPORE; BIOCHEMICAL STUDIES; CATALYTIC PROPERTIES; CYTOCHROME P450; DEGREE OF CONJUGATIONS; INTRAMOLECULAR CYCLIZATIONS; LONG TERM STABILITY; METABOLOMICS; STREPTOMYCES COELICOLOR;

CRYSTAL ORIENTATION; PORPHYRINS;

CYCLIZATION;

CYTOCHROME P450; CYTOCHROME P450 154A1; DIPENTAENONE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CRYSTAL STRUCTURE; CYCLIZATION; GENE DELETION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLOMICS; NONHUMAN; OXIDATION; REDUCTION; STREPTOMYCES COELICOLOR; ULTRAVIOLET RADIATION;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLIZATION; CYTOCHROME P-450 ENZYME SYSTEM; OXIDATION-REDUCTION; PENTANONES; STREPTOMYCES COELICOLOR;

EID: 78049407027     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja107801v     Document Type: Article

References (18)

1. Guengerich, F. P. Chem. Res. Toxicol. 2001, 14, 611-650
2. Ortiz de Montellano, P. R. Cytochrome P450: Structure, Mechanism, and Biochemistry; 3rd ed.; Kluwer Academic/Plenum Publishers: New York, 2005.
3. Bentley, S. D. Nature 2002, 417, 141-147
4. Lamb, D. C., Waterman, M. R., Kelly, S. L., and Guengerich, F. P. Curr. Opin. Biotechnol. 2007, 18, 504-512
5. Lamb, D. C., Guengerich, F. P., Kelly, S. L., and Waterman, M. R. Expert Opin. Drug Metab. Toxicol. 2006, 2, 27-40
6. Lamb, D. C., Skaug, T., Song, H. L., Jackson, C. J., Podust, L. M., Waterman, M. R., Kell, D. B., Kelly, D. E., and Kelly, S. L. J. Biol. Chem. 2002, 277, 24000-24005
7. Podust, L. M., Bach, H., Kim, Y., Lamb, D. C., Arase, M., Sherman, D. H., Kelly, S. L., and Waterman, M. R. Protein Sci. 2004, 13, 255-268
8. Kieser, T., Bibb, M. J., Buttner, M. J., Chater, F., and Hopwood, D. A. Practical Streptomyces Genetics; The John Innes Foundation: Norwich U.K., 2000.
9. Smith, C. A., Want, E. J., O'Maille, G., Abagyan, R., and Siuzdak, G. Anal. Chem. 2006, 78, 779-787
10. Katajamaa, M., Miettinen, J., and Oresic, M. Bioinformatics 2006, 22, 634-636
11. Corre, C. and Challis, G. L. ChemBioChem 2005, 6, 2166-2170
12. Aguilar, A. and Hopwood, D. A. J. Gen. Microbiol. 1982, 128, 1893-1901
13. Tius, M. A., Patterson, G. M., and Astrab, D. P. J. Antibiot. (Tokyo) 1985, 38, 1061-1067
14. Büchi, G., Inman, C. G., and Lipinsky, E. S. J. Am. Chem. Soc. 1954, 76, 4327-4331
15. Hecker, M. and Ullrich, V. J. Biol. Chem. 1989, 264, 141-150
16. Song, W. C. and Brash, A. R. Science 1991, 253, 781-784
17. Zhao, B., Lei, L., Vassylyev, D. G., Lin, X., Cane, D. E., Kelly, S. L., Yuan, H., Lamb, D. C., and Waterman, M. R. J. Biol. Chem. 2009, 284, 36711-36719
18. Yun, C. H., Ahn, T., Guengerich, F. P., Yamazaki, H., and Shimada, T. Arch. Biochem. Biophys. 1999, 367, 81-88