bis-cis-Dihydrodiols: A new class of metabolites resulting from biphenyl dioxygenase-catalyzed sequential asymmetric cis-dihydroxylation of polycyclic arenes and heteroarenes

Journal of Organic Chemistry

Volumn 64, Issue 11, 1999, Pages 4005-4011

  Boyd, Derek R ^a   Sharma, Narain D ^a   Hempenstall, Francis ^a   Kennedy, Martina A ^a   Malone, John F ^a   Allen, Christopher C R ^a   Resnick, Sol M ^b   Gibson, David T ^b  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

^b UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIHYDROXY 1,2 DIHYDROBENZO[B]NAPHTHO[2,1 D]THIOPHENE; 1,2,7,8 TETRAHYDROXY 1,2,7,8 TETRAHYDROBENZO[B]NAPHTHO[2,1 D]THIOPHENE; 3,4 DIHYDROXY 3,4 DIHYDROCHRYSENE; 3,4,9,10 TETRAHYDROXY 3,4,9,10 TETRAHYDROCHRYSENE; 9,10 DIHYDROXY 9,10 DIHYDROBENZO[C]PHENANTHRIDINE; BENZO[B]NAPHTHO[2,1 D]THIOPHENE; BENZO[C]PHENANTHRIDINE DERIVATIVE; BIPHENYL DERIVATIVE; CHRYSENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; HYDROXYLATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SPHINGOMONAS; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033612379     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982517n     Document Type: Article

References (22)

1. Nordqvist, M.; Thakker, D. R.; Vyas, K. P.; Yagi, H.; Levin, W.; Ryan, D. E.; Thomas, P. E.; Conney, A. H.; Jerina, D. M. Mol. Pharmacol. 1981, 19, 168.
2. Murphy, S. E.; Amin, S.; Coletta, K.; Hoffmann, D. Chem. Res. Toxicol. 1992, 5, 491.
3. Wenzel-Hartung, R.; Brune, H.; Grimmer, G.; Germann, P.; Timm, J.; Wosniok, W. Exp. Pathol. 1990, 40, 221.
4. Agarwal, S. K.; Boyd, D. R.; McGuckin, M. R.; Jennings, W. B.; Howarth, O. W. J. Chem. Soc., Perkin Tram. 1 1990, 3073.
5. Platt, K. L.; Reischmann, I. Mol. Pharmacol. 1987, 32, 710
6. Thakker, D. R.; Yagi, H. J.; Sayer, M.; Kapur, U.; Levin, W.; Chang, R. L.; Wood, A. W.; Conney, A. H.; Jerina, D. M. J. Biol. Chem. 1984, 260, 11249.
7. Boroujerdi, M.; Kung H. C.; Wilson A. G. E.; Anderson M. W. Cancer Res. 1981, 41, 951.
8. Glatt, H.; Seidel, A.; Ribeiro, O.; Kirkby, C.; Hirom P.; Oesch, F. Carcinogenesis 1987, 8, 1621.
9. Boyd, D. R.; Sharma, N. D.; Agarwal, R.; Resnick, S. M.; Schocken, M. J.; Gibson, D. T.; Sayer, J. M.; Yagi, H.; Jerina, D. M. J. Chem. Soc., Perkin Trans. 1 1997, 1715.
10. Jeffrey, A. M.; Yeh, H. J. C.; Jerina, D. M.; Patel, T. R.; Davey, J. F.; Gibson, D. T. Biochemistry 1975, 14, 575.
11. Boyd, D. R.; McMordie, R. A. S.; Porter, H. P.; Dalton, H.; Jenkins, R. O.; Howarth, O. J. Chem. Soc., Chem. Commun. 1987, 1722.
12. Jerina, D. M.; Selander H.; Yagi, H.; Wells, M. C.; Davey, J. F.; Mahadevan, V.; Gibson, D. T. J. Am. Chem. Soc. 1976, 98, 5988.
13. Akhtar, M. N.; Boyd, D. R. Thompson, N. J.; Koreeda, M.; Gibson, D. T.; Mahadevan, V.; Jerina, D. M. J. Chem. Soc., Perkin Trans. 1 1975, 2506.
14. Koreeda, M.; Akhtar, M. N.; Boyd, D. R.; Neill, J. D.; Gibson D. T. J. Org. Chem. 1978, 43, 1023.
15. Gibson, D. T.; Mahadevan, V.; Jerina, D. M.; Yagi, H.; Yeh, H. J. C. Science 1975, 189, 295.
16. Jerina, D. M.; van Bladeren, P. J.; Yagi, H.; Gibson, D. T.; Mahadevan, V.; Neese, A. S.; Koreeda, M.; Sharma, N. D.; Boyd D. R. J. Org. Chem. 1984, 49, 3621.
17. Gibson, D. T.; Subramanian, V. In Microbial Degradation of Organic Compounds; Gibson, D. T., Ed.; Marcel Dekker: New York, 1984; p 181.
18. Resnick, S. M.; Lee, K.; Gibson, D. T. J. Ind. Microbiol. 1996, 17, 438.
19. Boyd, D. R.; Sheldrake, G. N. Nat. Prod. Rep. 1998, 309.
20. Resnick, S. M.; Torok, D. S.; Gibson, D. T. J. Org. Chem. 1995, 60, 3546.
21. Hall, G. E.; Walker, J. Chem. Soc. 1968, 2237.
22. Sheldrick, G. M. SHELX-97, University of Göttingen, Germany 1997.