19F NMR study on the regiospecificity of hydroxylation of tetrafluoro- 4-hydroxybenzoate by wild-type and Y385F p-hydroxybenzoate hydroxylase: Evidence for a consecutive oxygenolytic dehalogenation mechanism

Biochemistry

Volumn 36, Issue 46, 1997, Pages 14192-14201

  Van Der Bolt, Frank J T ^a   Van Den Heuvel, Robert H H ^a   Vervoort, Jacques ^a   Van Berkel, Willem J H ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYBENZOATE 3 MONOOXYGENASE; HYDROXYBENZOIC ACID DERIVATIVE; 4 HYDROXYBENZOIC ACID ESTER; FLAVOPROTEIN; FLUORINE; ISOTOPE; OXYGEN; TETRAFLUORO 4 HYDROXYBENZOIC ACID; TETRAFLUORO-4-HYDROXYBENZOIC ACID;

ARTICLE; CANDIDA PARAPSILOSIS; CONTROLLED STUDY; DEFLUORINATION; ENZYME MECHANISM; ENZYME SPECIFICITY; ENZYME SUBSTRATE COMPLEX; HYDROXYLATION; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; BINDING SITE; CANDIDA; ENZYMOLOGY; METABOLISM; NUCLEAR MAGNETIC RESONANCE; SPECTROFLUOROMETRY; STEREOISOMERISM;

4-HYDROXYBENZOATE-3-MONOOXYGENASE; BINDING SITES; CANDIDA; FLAVOPROTEINS; FLUORINE; ISOTOPES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OXYGEN; PARABENS; SPECTROMETRY, FLUORESCENCE; STEREOISOMERISM;

EID: 0030613788     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi971213c     Document Type: Article

References (36)

1. Bolognesi, M., Ghisla, S., & Incoccia, L. (1978) Acta Crystallogr. B 34, 821-828.
2. Den Besten, C., van Bladeren, P. J., Duizer, E., Vervoort, J., & Rietjens, I. M. C. M. (1993) Chem. Res. Toxicol. 6, 674-680.
3. Entsch, B., & van Berkel, W. J. H. (1995) FASEB J. 9, 476-483.
4. Entsch, B., Ballou, D. P., & Massey, V. (1976a) J. Biol. Chem. 251, 2550-2563.
5. Entsch, B., Ballou, D. P., Husain, M., & Massey, V. (1976b) J. Biol. Chem. 251, 7367-7379.
6. Entsch, B., Palfey, B. A., Ballou, D. P., & Massey, V. (1991) J. Biol. Chem. 266, 17341-17349.
7. Eschrich, K., van der Bolt, F. J. T., de Kok, A., & van Berkel, W. J. H. (1993) Eur. J. Biochem. 216, 137-146.
8. Eppink, M. H. M., Schreuder, H. A., & van Berkel, W. J. H. (1995) Eur. J. Biochem. 231, 157-165.
9. Fetzner, S., & Lingens, F. (1994) Microbiol. Rev. 58, 641-685.
10. Gatti, D. L., Palfey, B. A., Lah, M. S., Entsch, B., Massey, V. Ballou, D. P., & Ludwig, M. L. (1994) Science 266, 110-114.
11. Gatti, D. L., Entsch, B., Ballou, D. P., & Ludwig, M. L. (1996) Biochemistry 35, 567-578.
12. Husain, M., Entsch, B., Ballou, D. P., Massey, V., & Chapman, P. (1980) J. Biol. Chem. 255, 4189-4197.
13. Lah, M. S., Palfey, B. A., Schreuder, H. A., & Ludwig, M. L. (1994) Biochemistry 33, 1555-1564.
14. Massey, V. (1994) J. Biol. Chem. 269, 22459-22462.
15. Peelen, S., Rietjens, I. M. C. M., van Berkel, W. J. H., van Workum, W. A. T., & Vervoort, J. (1993) Eur. J. Biochem. 218, 345-353.
16. Peelen, S., Rietjens, I. M. C. M., Boersma, M. G., & Vervoort, J. (1995) Eur. J. Biochem. 227, 284-291.
17. Rietjens, I. M. C. M., Soffers, A. E. M., Veeger, C., & Vervoort, J. (1993) Biochemistry 32, 4801-4812.
18. Rietjens, I. M. C. M., den Besten, C., Hanzlik, R. P., & van Bladeren, P. J. (1997) Chem. Res. Toxicol. 10, 629-635.
19. Schreuder, H. A., van der Laan, J. M., Hol, W. G. J., & Drenth, J. (1988) J. Mol. Biol. 199, 637-648.
20. Schreuder, H. A., Prick, P., Wierenga, R. K., Vriend, G., Wilson, K. S., Hol, W. G. J., & Drenth, J. (1989) J. Mol. Biol. 208, 679-696.
21. Schreuder, H. A., Hol, W. G. J., & Drenth, J. (1990) Biochemistry 29, 3101-3108.
22. Schreuder, H. A., van der Laan, J. M., Hol, W. G. J., & Drenth, J. (1991) in Chemistry and Biochemistry of Flavoenzymes (Müller, F., Ed.) Vol. 2, pp 31-64, CRC Press, Boca Raton.
23. Schreuder, H. A., van der Laan, J. M., Swarte, M. B. A., Kalk, K. H., Hol, W. G. J., & Drenth, J. (1992) Proteins 14, 178-190.
24. Schreuder, H. A., Mattevi, A., Obmolova, G., Kalk, K. H., Hol, W. G. J., van der Bolt, F. J. T., & van Berkel, W. J. H. (1994) Biochemistry 33, 10161-10170.
25. Stanier, R. Y., & Ornston, L. N. (1973) Adv. Microbiol. Physiol. 9, 89-151.
26. Suzuki, K., Gomi, T., Kaidoh, T., & Itagaki, E. (1991) J. Biochem. 109, 348-353.
27. van Berkel, W. J. H., & Müller, F. (1989) Eur. J. Biochem. 179, 307-314.
28. van Berkel, W. J. H., & Müller, F. (1991) in Chemistry and Biochemistry of Flavoenzymes (Müller, F., Ed.) Vol. 2, pp 1-29, CRC Press, Boca Raton.
29. van Berkel, W. J. H., Westphal, A. H., Eschrich, K., Eppink, M. H. M., & de Kok, A. (1992) Eur. J. Biochem. 210, 411-419.
30. van Berkel, W. J. H., Eppink, M. H. M., Middelhoven, W. J., Vervoort, J., & Rietjens, I. M. C. M. (1994) FEMS Microbiol. Lett. 121, 207-216.
31. van Berkel, W. J. H., Eppink, M. H. M., van der Bolt, F. J. T., Vervoort, J., Rietjens, I. M. C. M., & Schreuder, H. A. (1997) in Flavins and Flavoproteins XII (Stevenson, K., Massey, V., & Williams, Ch. Jr., Eds.) pp 305-314, Calgary University Press, Calgary.
32. Vervoort, J., Müller, F., Lee, J., van den Berg, W. A. M., & Moonen, C. T. W. (1986) Biochemistry 25, 8062-8067.
33. Vervoort, J., Rietjens, I. M. C. M., van Berkel, W. J. H., & Veeger, C. (1992) Eur. J. Biochem. 206, 479-484.
34. Wieser, M., Wagner, B., Eberspächer, J., & Lingens, F. (1997) J. Bacteriol. 179, 202-208.
35. Xun, L. (1996) J. Bacteriol. 178, 2645-2649.
36. Xun, L., Topp, E., & Orser, C. S. (1992) J. Bacteriol. 174, 5745-5747.