ipso-substitution: A general biochemical and biodegeneration mechanism to cleave α-quaternary alkylphenols and bisphenol A

Chemistry and Biodiversity

Volumn 4, Issue 9, 2007, Pages 2123-2137

  Gabriel, Frédéric L P ^a   Cyris, Maike ^a   Giger, Walter ^a   Kohler, Hans Peter E ^a  

^a SWISS FEDERAL INSTITUTE OF AQUATIC SCIENCE AND TECHNOLOGY   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 HYDROXYPHENYL)ISOPROPANOL; 4 HYDROXY 4 ISOPROPENYLCYCLOHEXA 2,5 DIEN 1 ONE; 4 HYDROXY 4 ISOPROPYLCYCLOHEXA 2,5 DIEN 1 ONE; 4 ISOPROPENYLPHENOL; 4 ISOPROPYLPHENOL; 4,4' ISOPROPYLIDENEDIPHENOL; ALKYLPHENOL; HYDROQUINONE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL CELL; BACTERIAL METABOLISM; BACTERIAL STRAIN; BACTERIUM; BIOCHEMISTRY; BIODEGRADATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; INCUBATION TIME; MASS SPECTROMETRY; METABOLITE; NONHUMAN; SPHINGOBIUM XENOPHAGUM; ULTRAVIOLET SPECTROSCOPY;

BIODEGRADATION, ENVIRONMENTAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; PHENOLS; SPHINGOMONAS;

BACTERIA (MICROORGANISMS); SPHINGOBIUM;

EID: 34948876976     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.200790170     Document Type: Article

References (40)

1. C. Sonnenschein, A. M. Soto, J. Steroid Biochem. Molec. Biol. 1998, 65, 143.
2. K. Guenther, V. Heinke, B. Thiele, E. Kleist, H. Prast, T. Raecker, Environ. Sci. Technol. 2002, 36, 1676.
3. A. M. Soto, H. Justicia, J W. Wray, C. Sonnenschein, Environ. Health Perspect. 1991, 92, 167.
4. M. R. Servos, Water Qual. Res. J. Canada 1999, 34, 123.
5. B.-J. Nira, R. Steinmetz, Trends Endocrinol. Metab. 1998, 9, 124.
6. G. M. Gray, J. T Cohen, G. Cunha, C. Hughes, E. E. McConell, L. Rhomberg, I. G. Sipes, D. Mattison, Hum. Ecol. Risk Assess. 2004, 10, 875.
7. F. L. P. Gabriel, A. Heidlberger, D. Rentsch, W. Giger, K. Guenther, H.-P. E. Kohler, J. Biol. Chem. 2005, 280, 15526.
8. P. F. X. Corvini, J. Hollender, R. Ji, S. Schumacher, J. Prell, G. Hommes, U. Priefer, R. Vinken, A. Schäffer, Appl. Microbiol. Biotechnol. 2006, 70, 114.
9. T. Ohe, M. Hirobe, T. Mashino, Drug Metab. Dispos. 2000, 28, 110.
10. T. Ohe, T. Mashino, M. Hirobe, Drug Metab. Dispos. 1997, 25, 116.
11. F. P. Guengerich, Chem. Res. Toxicol. 2001, 14, 611.
12. J. G. Traynham, J. Chem. Educ. 1983, 60, 937.
13. F. L. P. Gabriel, W Giger, K. Guenther, H.-P. E. Kohler, Appl. Environ. Microbiol. 2005, 71, 1123.
14. F. L. P. Gabriel, M. Cyris, N. Jonkers, W Giger, K. Guenter, H.-P. E. Kohler, Appl. Environ. Microbiol. 2007, 73, 3320.
15. J. Spivack, T. K. Leib, J. H. Lobos, J. Biol. Chem. 1994, 269, 7323.
16. J.-H. Kang, Y. Katayama, F Kondo, Toxicology 2006, 217, 81.
17. R. H. Schuler, G. Albarran, J. Zajicek, M. V. George, R. W. Fessenden, I. Carmichael, J Phys. Chem. A 2002, 106, 12178.
18. K. P. Vatsis, M. J. Coon, Arch. Biochem. Biophys. 2002, 397, 119.
19. Y.-S. Shaw, C. Chen, Biochem. J. 1972, 128, 1285.
20. J. A. Thompson, A. M. Malkinson, M. D. Wand, S. L. Mastovich, E. W Mead, K. M. Schullek, W. G. Laudenschlager, Drug Metab. Dispos. 1987, 5, 833.
21. B. Ajithkumar, V. P. Ajithkumar, R. Iriye, Res. Microbiol. 2003, 154, 17.
22. K. Hultzsch, 'Chemie der Phenolharze', Springer-Verlag, Berlin-Göttingen-Heidelberg, 1950, p. 27.
23. R. H. H. van den Heuvel, M. W. Fraaije, W. J. H. van Berkel, FEBS Lett. 2000, 481, 109.
24. H. Furukawa, M. Wieser, H. Morita, T. Sugio, T. Nagasawa, Arch. Microbiol. 1998, 171, 37.
25. D. J. Hopper, L. Cottrell, Appl. Environ. Microbiol. 2003, 69, 3650.
26. T. Fukuda, H. Uchida, M. Suzuki, H. Miyamoto, H. Morinaga, H. Nawata, T. Uwajima, J. Chem. Technol. Biotechnol. 2004, 79, 1212.
27. J. Michizoe, H. Ichinose, N. Kamiya, T. Maruyama, M. Goto, J. Biosci. Bioeng. 2005, 99, 642.
28. T. Hirano, Y. Honda, T. Watanabe, M. Kuwahara, Biosci. Biotechnol. Biochem. 2000, 64, 1958.
29. H. Sakuyama, Y. Endo, K. Fujimoto, Y. Hatano, J. Biosci. Bioeng. 2003, 96, 227.
30. W. Chai, H. Sakamaki, S. Kitanaka, M. Saito, C. A. Horiuchi, Biosci. BiotechnoL Biochem. 2003,67, 218.
31. S. Yoshihara, T. Mizutare, M. Makishima, N. Suzuki, N. Fujimoto, K. Igarashi, S. Ohta, Toxicol. Sci. 2004, 78, 50.
32. M. Chivukula, V. Renganathan, Appl. Environ. Microbiol. 1995, 61, 4374.
33. P. J. Kersten, B. Kalyanaraman, K. E. Hammel, B. Reinhammar, T. K. Kirk, Biochem. J. 1990, 268, 475.
34. K. Valli, H. Wariishi, M. H. Gold, J Bacteriol. 1992, 174, 2131.
35. M. Sasaki, J.-i. Maki, K.-i. Oshiman, Y. Matsumura, T. Tsuchido, Biodegradation 2005, 16, 449.
36. M. Sasaki, A. Akahira, K.-i. Oshiman, T. Tsuchido, Y. Matsumura, Appl. Environ. Microbiol. 2005, 71, 8024.
37. Z. Ronen, A. Abeliovich, Appl. Environ. Microbiol. 2000, 66, 2372.
38. H. Cabana, J.-L. H. Jiwan, R. Rozenberg, V Elisashvili, M. Penninckx, S. N. Agathos, J. P. Jones, Chemosphere 2007, 67, 770.
39. K. Sakai, H. Yamanaka, K. Moriyoshi, T. Ohmoto, T. Ohe, Biosci. Biotechnol. Biochem. 2007, 71, 60351-1-7.
40. B. Kolvenbach, N. Schlaich, Z. Raoui, J. Prell, S. Zühlke, A. Schäffer, F. P. Guengerich, P. F. X. Corvini, Appl. Environ. Microbiol. 2007, 73, 4776.