Purification and properties of 4-hydroxybenzoate 1-hydroxylase (decarboxylating), a novel flavin adenine dinucleotide-dependent monooxygenase from Candida parapsilosis CBS604

Journal of Bacteriology

Volumn 179, Issue 21, 1997, Pages 6680-6687

  Eppink, Michel H M ^a   Boeren, Sjef A ^a   Vervoort, Jacques ^a   Van Berkel, Willem J H ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

FLAVINE ADENINE NUCLEOTIDE; UNSPECIFIC MONOOXYGENASE;

ARTICLE; CANDIDA PARAPSILOSIS; CATALYSIS; DECARBOXYLATION; ENZYME ACTIVITY; ENZYME PURIFICATION; ENZYME SPECIFICITY; PRIORITY JOURNAL; STOICHIOMETRY;

CANDIDA PARAPSILOSIS;

EID: 0030690286     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/jb.179.21.6680-6687.1997     Document Type: Article

References (39)

1. Anderson, J. J., and S. Dagley. 1980. Catabolism of aromatic acids in Trichosporon cutaneum. J. Bacteriol. 141:534-543.
2. Brodie, B. B., and J. Axelrod. 1948. The estimation of acetanilide and its metabolic products, aniline, N-acetyl p-aminophenol and p-aminophenol (free and conjugated) in biological fluids and tissues. J. Pharmacol. Exp. Ther. 94:22-28.
3. Buswell, J. A., K.-E. Eriksson, and B. Petterson. 1981. Purification and partial characterization of vanillate hydroxylase (decarboxylating) from Sporotrichium pulverulentum. J. Chromatogr. 215:99-108.
4. Cain, R. B., R. F. Bilton, and J. A. Darrah. 1968. The metabolism of aromatic acids by microorganisms: metabolic pathways in the fungi. Biochem. J. 108: 797-828.
5. Crawford, R. L. 1975. Novel pathway for degradation of protocatechuic acid in Bacillus species. J. Bacteriol. 121:531-536.
6. Entsch, B., and W. J. H. van Berkel. 1995. Structure and mechanism of p-hydroxybenzoate hydroxylase. FASEB J. 9:476-483.
7. Eschrich, K., F. J. T. van der Bolt, A. de Kok, and W. J. H. van Berkel. 1993. Role of Tyr201 and Tyr385 in substrate activation hy p-hydroxybenzoate hydroxylase from Pseudomonas fluorescens. Eur. J. Biochem. 216:137-146.
8. Fieser, L. F., and M. Fieser. 1967. Reagents for organic synthesis, vol. I. John Wiley & Sons, Ltd., London.
9. Fraaije, M. W., A. Mattevi, and W. J. H. van Berkel. 1997. Mercuration of vanillyl-alcohol oxidase from Penicillium simplicissimum generates inactive dimers. FEBS Lett. 402:33-35.
10. Fraaije, M. W., M. Pikkemaat, and W. J. H. van Berkel. 1997. Enigmatic gratuitous induction of the covalent flavoprotein vanillyl-alcohol oxidase in Penicillium simplicissimum. Appl. Environ. Microbiol. 63:435-439.
11. Gaal, A., and H. Y. Neujahr. 1979. Metabolism of phenol and resorcinol in Trichosporon cutaneum. J. Bacteriol. 137:13-21.
12. Gaal, A., and H. Y. Neujahr. 1981. Induction of phenol-metabolizing enzymes in Trichosporon cutaneum. Arch. Microbiol. 130:54-58.
13. Hareland, W. A., R. L. Crawford, P. J. Chapman, and S. Dagley. 1975. Metabolic function and properties of 4-hydroxyphenylacetic acid 1-hydroxylase from Pseudomonas acidovorans. J. Bacteriol. 121:272-285.
14. Husain, M., B. Entsch, D. P. Ballou, V. Massey, and P. J. Chapman. 1980. Fluoride elimination from substrates in hydroxylation reactions catalyzed by p-hydroxybenzoate hydroxylase. J. Biol. Chem. 255:4189-4197.
15. Komiyama, M., and H. Hirai. 1984. Selective synthesis using cyclodextrins as catalysts. 2. Para-oriented carboxylation of phenols. J. Am. Chem. Soc. 106:174-178.
16. Massey, V. 1994. Activation of molecular oxygen by flavins and flavoproteins. J. Biol. Chem. 269:22459-22462.
17. Middelhoven, W. J., A. Coenen, B. Kraakman, and M. D. Sollewijn Gelpke. 1992. Degradation of some phenols and hydroxybenzoates by the imperfect ascomycetous yeasts Candida parapsilosis and Arxula adeninivorans: evidence for an operative gentisate pathway. Antonie Leeuwenhoek 62:181-187.
18. Middelhoven, W. J. 1993. Catabolism of benzene compounds by ascomycetous and basidiomycetous yeasts and yeastlike fungi. Antonie Leeuwenhoek 63:125-144.
19. Neujahr, H. Y., and A. Gaal. 1973. Phenol hydroxylase from yeast: purification and properties of the enzyme from Trichosporon cutaneum. Eur. J. Biochem. 35:386-400.
20. Neujahr, H. Y. 1983. Effects of anions, chaotropes and phenol on the attachment of flavin adenine dinucleotide to phenol hydroxylase. Biochemistry 22:580-584.
21. Ornston, L. N., and R. Y. Stanier. 1966. The conversion of catechol and protocatechuate to β-ketoadipate by Pseudomonas putida. J. Biol. Chem. 241:3776-3786.
22. 19F-NMR study on the pH-dependent regioselectivity and rate of the ortho-hydroxyiation of 3-fluorophenol by phenol hydroxylase from Trichosporon cutaneum. Implications for the reaction mechanism. Eur. J. Biochem. 218:345-353.
23. Peelen, S., I. M. C. M. Rietjens, M. G. Boersma, and J. Vervoort. 1995. Conversion of phenol derivatives to hydroxylated products by phenol hydroxylase from Trichosporon cutaneum. Eur. J. Biochem. 227:284-291.
24. Peterson, G. L. 1977. A simplification of the protein assay method of Lowry et al. which is more generally applicable. Anal. Biochem. 83:346-356.
25. Seibold, B., M. Matthes, M. H. M. Eppink, F. Lingens, W. J. H. van Berkol, and R. Müller. 1996. 4-Hydroxybenzoate hydroxylase from Pseudomonas sp. CBS3. Eur. J. Biochem. 239:469-478.
26. Stanier, R. Y., and L. N. Ornston. 1973. The β-ketoadipate pathway. Adv. Microb. Physiol. 9:89-151.
27. Suzuki, K., and M. Itoh. 1986. Metabolism of p-hydroxybenzoate via hydroxyquinol by Trichosporon cutaneum WY2-2: characterization of the pathway using superoxide dismutase as a stabilizer of hydroxyquinol. Plant Cell Physiol. 27:1451-1460.
28. Tsuji, H., T. Ogawa, N. Bando, and K. Sasaoko. 1986. Purification and properties of 4-aminobenzoate hydroxylase, a new monooxygenase from Agaricus bisporus. J. Biol. Chem. 261:13203-13209.
29. Van Berkel, W. J. H., and W. J. J. van den Tweel. 1991. Purification and characterisation of 3-hydroxyphenylacetate 6-hydroxylase: a novel FAD-dependent monooxygenase from a Flavobacterium species. Eur. J. Biochem. 201:585-592.
30. Van Berkel, W. J. H., M. H. M. Eppink, W. J. Middelhoven, J. Vervoort, and I. M. C. M. Rietjens. 1994. Catabolism of 4-hydroxybenzoate in Candida parapsilosis proceeds through initial oxidative decarboxylation by a FAD-dependent 4-hydroxybenzoate 1-hydroxylase. FEMS Microbiol. Lett. 121: 207-216.
31. Van Berkel, W. J. H., M. H. M. Eppink, F. J. T. van der Bolt, J. Vervoort, I. M. C. M. Rietjens, and H. A. Schreuder. 1997. p-Hydroxybenzoate hydroxylase: mutants and mechanism, I, p. 305-314. In K. Stevenson, V. Massey, and C. H. Williams, Jr. (ed.), Flavins and flavoproteins XII, in press. University Press, Calgary, Canada.
32. Van Berkel, W. J. H., K. Ruiter, M. H. M. Eppink, and J. Vervoort. 1997. Substrate specificity of 4-hydroxybenzoate 1-hydroxylase from Candida parapsilosis, p. 399-402. In K. Stevenson, V. Massey, and C. H. Williams, Jr. (ed.), Flavins and flavoproteins XII, in press. University Press, Calgary, Canada.
33. Vervoort, J., I. M. C. M. Rietjens, W. J. H. van Berkel, and C. Veeger. 1992. Frontier orbital study on the 4-hydroxybenzoate-3-hydroxylase-dependent activity with benzoate derivatives. Eur. J. Biochem. 206:479-484.
34. Vervoort, J., L. Ridder, W. J. H. van Berkel, and I. M. C. M. Rietjens. 1997. Flavoprotein monooxygenases: mechanistic overview, p. 281-292. In K. Stevenson, V. Massey and C. H. Williams, Jr. (ed.), Flavins and flavoproteins XII, in press. University Press, Calgary, Canada.
35. Vogel, A. I. 1989. Textbook of practical organic chemistry, 5th ed. Longman, London.
36. White-Stevens, R. H., and H. Kamin. 1972. Studies of a flavoprotein, salicylate hydroxylase. J. Biol. Chem. 247:2358-2370.
37. Wright, J. D. 1993. Fungal degradation of benzoic acid and related compounds. World J. Microbiol. Biotechnol. 9:9-16.
38. Wright, J. D., and C. Ratledge. 1991. Isolation of two Rhodotorula rubra strains showing differences in the degradation of aromatic compounds. Appl. Microbiol. Biotechnol. 35:94-99.
39. Xun, L. 1996. Purification and characterization of chlorophenol 4-monooxygenase from Burkholderia cepacia AC1100. J. Bacteriol. 178:2645-2649.