Dihydrodiols from Anthracene and Phenanthrene

Journal of the American Chemical Society

Volumn 98, Issue 19, 1976, Pages 5988-5996

  Jerina, D M ^a,b,c   Selander, H ^a,b,c   Yagi, H ^a,b,c   Wells, Martha C ^a,b,d   Davey, J F ^a,b,d   Mahadevan, V ^a,b,d   Gibson, D T ^a,b,d  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^c NIAMDD ^*  (United States)

^d UNIVERSITY OF TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE DERIVATIVE; GLYCOL; PHENANTHRENE DERIVATIVE;

ARTICLE; AZOTOBACTER; BIOSYNTHESIS; METABOLISM; PSEUDOMONAS;

ANTHRACENES; AZOTOBACTER; GLYCOLS; PHENANTHRENES; PSEUDOMONAS;

EID: 0017307965     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00435a035     Document Type: Article

References (56)

1. A. M. Jeffrey, H. J. C. Yeh, D. M. Jerina, T. R. Patel, J. F. Davey, and D. T. Gibson, Biochemistry, 14, 575 (1975).
2. D. M. Jerina and J. W. Daly, Science, 185, 573 (1974).
3. D. T. Gibson, Crit. Rev. Microbiol., 1, 199 (1971).
4. L. Young, Biochem. J., 41, 417 (1947).
5. E. Boyland and G. Wolf, Biochem. J., 47, 64 (1950).
6. R. Criegee, B. Marchand, and H. Wannowius, Justus Leibigs Ann. Chem., 550, 99 (1942).
7. E. D. S. Corner and L. Young, Biochem. J., 61, 132 (1955).
8. E. Boyland and P. Sims, Biochem. J., 84, 571 (1962).
9. P. Sims, Biochem. Pharmacol., 19, 795 (1970).
10. C. Colla, C. Biaggi, and V. Treccani, Rend. Accad. Naz. Lincei, 23, 66 (1957).
11. W. C. Evans, H. N. Fernley, and E. Griffiths, Biochem. J., 95, 819 (1965).
12. E. Boyland and A. A. Levi, Biochem. J., 29, 2679 (1935).
13. P. Sims, Biochem. J., 92, 621 (1964).
14. C. Colla, A. Fiecchi, and V. Treccani, Ann. Microbiol. Enzimol., 9, 1 (1959).
15. M. Karplus, J. Am. Chem. Soc., 85, 2870 (1963).
16. L. M. Jackman and S. Sternhell. “Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry”, 2d ed, Pergamon Press, New York, N.Y., 1969, pp 280-304, 334-341.
17. J. Booth, E. Boyland, and E. E. Turner, J. Chem. Soc., 1188 (1950).
18. S. H. Goh and R. G. Harvey. J. Am. Chem. Soc., 95, 242 (1973).
19. E. Boyland and D. Manson. J. Chem. Soc., 1837 (1951).
20. A. M. Jeffrey, H. J. C. Yeh, and D. M. Jerina, J. Org. Chem., 39, 1405 (1974).
21. D. T. Gibson, V. Mahadevan, D. M. Jerina, H. Yagi, and H. J. C. Yeh, Science, 189, 295 (1975).
22. D. J. McCaustland and J. F. Engle, Tetrahedron Lett., 2549 (1975).
23. D. T. Gibson, R. L. Roberts, H. C. Wells, and V. M. Kobal, Biochem. Biophys. Res. Commun., 50, 211 (1973).
24. M. N. Akhtar, N. J. Thompson, D. R. Boyd, M. Koreeda, D. T. Gibson, V. Mahadwan, and D. M. Jerina, J. Chem. Soc., Perkin Trans. 1, 2506 (1975).
25. K. D. Bartle and D. W. Jones, Adv. Org. Chem., 8, 317-424 (1972).
26. G. M. Badger, J. Chem. Soc., 2497 (1949).
27. P. Y. Bruice, T. C. Bruice, P. M. Dansette, H. G. Selander, H. Yagi, and D. M. Jerina, J. Am. Chem. Soc., 98, 2965 (1976).
28. A. S. Perlin, Oxidation, 1, 196 (1969).
29. W. C. Herndon, Trans. N. Y. Acad. Sci., 38, 200 (1974).
30. E. D. Becker, “High Resolution NMR”, Academic Press, New York, N.Y., 1969, p 104.
31. P. Y. Bruice, T. C. Bruice, H. Yagi, and D. M. Jerina, J. Am. Chem. Soc., 98, 2973 (1976).
32. R. Miura, S. Honmaru, and M. Nakazaki, Tetrahedron Lett., 5271 (1968).
33. H. Joshua, R. Gans, and K. Mislow, J. Am. Chem. Soc., 90, 4884 (1968).
34. P. Dansette and D. M. Jerina, J. Am. Chem. Soc., 96, 1224 (1974).
35. R. G. Harvey, S. H. Goh, and C. Cortez, J. Am. Chem. Soc., 97, 3468 (1975).
36. P. M. Dansette, H. Yagi, D. M. Jerina, J. W. Daly, W. Levin, A. Y. H. Lu, R. Kuntzman, and A. H. Conney, Arch. Biochem. Biophys., 164, 517 (1974).
37. D. M. Jerina, H. Yagi, and J. W. Daly, Heterocycles, 1, 267 (1973).
38. P. Sims, Biochem. J., 84, 558 (1962).
39. H. Yagi, G. M. Holder, P. M. Dansette, O. Hernandez, H. J. C. Yeh, R. A. LeMahieu, and D. M. Jerina, J. Org. Chem., 41, 977 (1976).
40. M. S. Newman and D. R. Olson. J. Am. Chem. Soc., 96, 6207 (1974).
41. G. Holder, H. Yagi, P. Dansette, D. M. Jerina, W. Levin, A. Y. H. Lu, and A. H. Conney, Proc. Natl. Acad. Sci. U.S.A., 71, 4356 (1974).
42. H. Yagi, O. Hernandez, and D. M. Jerina, J. Am. Chem. Soc., 97, 6881 (1975).
43. P. Sims, P. L. Grover, A. Swaisland, K. Pal, and A. Hewer, Nature (London), 252, 326 (1974).
44. E. Mosettig and H. M. Duvall, J. Am. Chem. Soc., 59, 367 (1937).
45. L. A. Fieser, J. Am. Chem. Soc., 51, 2460 (1929).
46. H. Yagi and D. M. Jerina, J. Am. Chem. Soc., 95, 243 (1973).
47. V. M. Micovic and M. L. Mihailovic, J. Org. Chem., 18, 1190 (1953).
48. L. A. Fieser, J. Am. Chem. Soc., 51, 1896 (1929).
49. L. A. Fieser, J. Am. Chem. Soc., 51, 940 (1929).
50. A. Y. H. Lu and M. J. Coon, J. Biol. Chem., 243, 1331 (1968).
51. A. Y. H. Lu, K. W. Junk, and M. J. Coon, J. Biol. Chem., 244, 3714 (1969).
52. F. Oesch, D. M. Jerina, and J. W. Daly, Biochem. Biophys. Acta, 227, 685 (1971).
53. M. J. Cook, A. R. Katritsky, F. C. Pennington, and B. M. Semple, J. Chem. Soc. B, 523 (1969).
54. M. J. Cook and N. L. Dassanyake, J. Chem. Soc., Perkin Trans. 2, 1901 (1972).
55. P. B. D. de la Mare, A. Singh, E. A. Johnson, R. Koenigsberger, J. S. Lomas, V. Sanchez del Olmo, and A. M. Sexton, J. Chem. Soc. B, 717 (1969).
56. G. W. Burton, M. D. Carr, P. B. D. de la Mare, and M. J. Rosser, J. Chem. Soc., Perkin Trans. 2, 710 (1972).