Spectral and catalytic properties of aryl-alcohol oxidase, a fungal flavoenzyme acting on polyunsaturated alcohols

Biochemical Journal

Volumn 389, Issue 3, 2005, Pages 731-738

  Ferreira, Patricia ^a   Medina, Milagros ^b   Guillén, Francisco ^a,d   Martínez, María Jesús ^a   Van Berkel, Willem J H ^c   Martínez, Ángel T ^a  

^a CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

^c WAGENINGEN UNIVERSITY   (Netherlands)

^d UNIVERSITY OF ALCALÁ   (Spain)

Author keywords

Aryl alcohol oxidase; Conjugated double bond; Flavoenzyme; Reaction mechanism; Substrate binding

Indexed keywords

BENZENE; CATALYSIS; ENZYMES; OXIDATION; THERMODYNAMIC STABILITY;

ARYL-ALCOHOL OXIDASE; CONJUGATED DOUBLE BOND; FLAVOENZYME; REACTION MECHANISM; SUBSTRATE BINDING;

ALCOHOLS;

ALCOHOL; ALCOHOL OXIDASE; COMPLEMENTARY DNA; FLAVOPROTEIN; FUNGAL ENZYME; METHANOL;

ARTICLE; BASIDIOMYCETES; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME PURIFICATION; ENZYME SUBSTRATE; FUNGUS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLEUROTUS; PRIORITY JOURNAL;

ALCOHOL OXIDOREDUCTASES; ALCOHOLS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PLEUROTUS;

PLEUROTUS ERYNGII;

EID: 23644451045     PISSN: 02646021     EISSN: None     Source Type: Journal    
DOI: 10.1042/BJ20041903     Document Type: Article

References (40)

1. Farmer, V. C., Henderson, M. E. K. and Russell, J. D. (1960) Aromatic-alcohol-oxidase activity in the growth medium of Polystictus versicolor. Biochem. J. 74, 257-262
2. Bourbonnais, R. and Paice, M. G. (1988) Veratryl alcohol oxidases from the lignin degrading basidiomycete Pleurotus sajor-caju. Biochem. J. 255, 445-450
3. Sannia, G., Limongi, P, Cocca, E., Buonocore, E, Nitti, G. and Giardina, P. (1991) Purification and characterization of a veratryl alcohol oxidase enzyme from the lignin degrading basidiomycete Pleurotus ostreatus. Biochim. Biophys. Acta 1073, 114-119
4. Varela, E., Böckle, B., Romero, A., Martínez, A. T. and Martínez, M. J. (2000) Biochemical characterization, cDNA cloning and protein crystallization of aryl-alcohol oxidase from Pleurotus pulmonarius. BBA Protein Struct. Mol. Enzym. 1476, 129-138
5. Guillén, F., Martínez, A. T. and Martínez, M. J. (1990) Production of hydrogen peroxide by aryl-alcohol oxidase from the ligninolytic fungus Pleurotus eryngii. Appl. Microbiol. Biotechnol. 32, 465-469
6. Muheim, A., Waldner, R., Leisola, M. S. A. and Fiechter, A. (1990) An extracellular arylalcohol oxidase from the white-rot fungus Bjerkandera adusta. Enzyme Microb. Technol. 12, 204-209
7. Goetghebeur, M., Nicolas, M., Brun, S. and Galzy, P. (1992) Production and excretion of benzyl alcohol oxidase in Botrytis cinerea. Phytochemistry 31, 413-416
8. Regalado, V., Perestelo, E, Rodríguez, A., Carnicero, A., Sosa, F. J., de la Fuente, G. and Falcon, M. A. (1999) Activated oxygen species and two extracellular enzymes: laccase and aryl-alcohol oxidase, novel for the lignin-degrading fungus Fusarium proliferatum. Appl. Microbiol. Biotechnol. 51, 388-390
9. Kim, S. J., Suzuki, N., Uematsu, Y. and Shoda, M. (2001) Characterization of aryl alcohol oxidase produced by dye-decolorizing fungus, Geotrichum candidum Dec1. J. Biosci. Bioeng. 91, 166-172
10. Gutiérrez, A., Caramelo, L., Prieto, A., Martínez, M. J. and Martínez, A. T. (1994) Anisaldehyde production and aryl-alcohol oxidase and dehydrogenase activities in ligninolytic fungi from the genus Pleurotus. Appl. Environ. Microbiol. 60, 1783-1788
11. 2 production by Pleurotus eryngii. Appl. Environ. Microbiol. 60, 2811-2817
12. Guillén, F., Martínez, A. T., Martínez, M. J. and Evans, C. S. (1994) Hydrogen peroxide-producing system of Pleurotus eryngii involving the extracellular enzyme aryl-alcohol oxidase. Appl. Microbiol. Biotechnol. 41, 465-470
13. Guillén, F., Martínez, A. T. and Martínez, M. J. (1992) Substrate specificity and properties of the aryl-alcohol oxidase from the ligninolytic fungus Pleurotus eryngii. Eur. J. Biochem. 209, 603-611
14. Hefti, M. H., Vervoort, J. and van Berkel, W. J. H. (2003) Deflavination and reconstitution of flavoproteins - tackling fold and function. Eur. J. Biochem. 270, 4227-4242
15. Varela, E., Martínez, A. T. and Martínez, M. J. (1999) Molecular cloning of aryl-alcohol oxidase from Pleurotus eryngii, an enzyme involved in lignin degradation. Biochem. J. 341, 113-117
16. Zamocky, M., Hallberg, M., Ludwig, R., Divne, C. and Haltrich, D. (2004) Ancestral gene fusion in cellobiose dehydrogenases reflects a specific evolution of GMC oxidoreductases in fungi. Gene 338, 1-14
17. Fraaije, M. W., van Berkel, W. J. H., Benen, J. A. E., Visser, J. and Mattevi, A. (1998) A novel oxidoreductase family sharing a conserved FAD-binding domain. Trends Biochem. Sci. 23, 206-207
18. Wierenga, R. K., Terpstra, P. and Hol, W. G. L. (1986) Prediction of the occurrence of the ADP-binding βαβ-fold in proteins, using an amino acid sequence fingerprint. J. Mol. Biol. 187, 101-107
19. Hecht, H. J., Kalisz, H. M., Hendle, J., Schmid, R. D. and Schomburg, D. (1993) Crystal structure of glucose oxidase from Aspergillus niger refined at 2.3 Å resolution. J. Mol. Biol. 229, 153-172
20. Varela, E., Guillén, F., Martínez, A. T. and Martínez, M. J. (2001) Expression of Pleurotus eryngii aryl-alcohol oxidase in Aspergillus nidulans: purification and characterization of the recombinant enzyme. Biochim. Biophys. Acta 1546, 107-113
21. Ferreira, P., Guillén, F., Ruiz-Dueñas, F. J., García de Lacoba, M., Martínez, M. J., van Berkel, W. J. H. and Martínez, A. T. (2002) Structure-function studies on fungal aryl-alcohol oxidase. In Flavins and Flavoproteins (Chapman, S. K., Perham, R. N. and Scrutton, N. S., eds.), pp. 155-160, Rudolf Weber, Berlin
22. Fernández-Cañón, J. M. and Peñalva, M. A. (1995) Overexpression of two penicillin structural genes in Aspergillus nidulans. Mol. Gen. Genet. 246, 110-118
23. de Jong, E., Cazemier, A. E., Field, J. A. and de Bont, J. A. M. (1994) Physiological role of chlorinated aryl alcohols biosynthesized de novo by the white rot fungus Bjerkandera sp strain BOS55. Appl. Environ. Microbiol. 60, 271-277
24. 19F NMR study on the biological Baeyer-Villiger oxidation of acetophenones. J. Ind. Microbiol. Biotechnol. 26, 35-42
25. Macheroux, P. (1999) UV-visible spectroscopy as a tool to study flavoproteins. In Flavoprotein Protocols (Chapman, S. K. and Reid, G. A., eds.), pp. 1-7, Humana Press, Totowa
26. Massey, V. (2000) The chemical and biological versatility of riboflavin. Biochem. Soc. Trans. 28, 283-296
27. Fraaije, M. W. and Mattevi, A. (2000) Flavoenzymes: diverse catalysts with recurrent features. Trends Biochem. Sci. 25, 126-132
28. Mattevi, A., Fraaije, M. W., Mozzarelli, A., Olivi, L., Coda, A. and van Berkel, W. J. H. (1997) Crystal structures and inhibitor binding in the octameric flavoenzyme vanillyl-alcohol oxidase: the shape of the active-site cavity controls substrate specificity. Structure 5, 907-920
29. De Sa, R. J. (1972) Putrescine oxidase from Micrococcus rubens. Purification and properties of the enzyme. J. Biol. Chem. 247, 5527-5534
30. Binda, C., Newton-Vinson, P., Hubalek, F., Edmondson, D. E. and Mattevi, A. (2002) Structure of human monoamine oxidase B, a drug target for the treatment of neurological disorders. Nat. Struct. Biol. 9, 22-26
31. Varela, E., Martínez, M. J. and Martínez, A. T. (2000) Aryl-alcohol oxidase protein sequence: a comparison with glucose oxidase and other FAD oxidoreductases. Biochim. Biophys. Acta 1481, 202-208
32. Wohlfahrt, G., Witt, S., Hendle, J., Schomburg, D., Kalisz, H. M. and Hecht, H.-J. (1999) 1.8 and 1.9 Å resolution structures of the Penicillium amagasekiense and Aspergillus niger glucose oxidase as a basis for modelling substrate complexes. Acta Crystallogr. Sect. D Biol. Crystallogr. 55, 969-977
33. Fraaije, M. W. and van Berkel, W. J. H. (1997) Catalytic mechanisms of the oxidative demethoxylation of 4-(methoxymethyl)phenol by vanillyl-alcohol oxidase. Evidence for formation of a p-quinone methide intermediate. J. Biol. Chem. 272, 18111-18116
34. Hopkins, T. R. (1985) A multipurpose enzyme sensor based on alcohol oxidase. Intern. Biotechnol. Lab. December, 20-25
35. Panoutsopoulos, G. I. and Beedham, C. (2004) Kinetics and specificity of guinea pig liver aldehyde oxidase and bovine milk xanthine oxidase towards substituted benzaldehydes. Acta Biochim. Pol. 51, 649-663
36. Miller, J. R. and Edmondson, D. E. (1999) Structure-activity relationships in the oxidation of para-substituted benzylamine analogues by recombinant human liver monoamine oxidase A. Biochemistry 38, 13670-13683
37. Fraaije, M. W., Veeger, C. and van Berkel, W. J. H. (1995) Substrate specificity of flavin-dependent vanillyl-alcohol oxidase from Penicillium simplicissimum. Evidence for the production of 4-hydroxycinnamyl alcohols from allylphenols. Eur. J. Biochem. 234, 271-277
38. Weibel, M. K. and Bright, H. J. (1971) The glucose oxidase mechanism. Interpretation of the pH dependence. J. Biol. Chem. 246, 2734-2744
39. Witt, S., Wohlfahrt, G., Schomburg, D., Hecht, H. J. and Kalisz, H. M. (2000) Conserved arginine-516 of Penicillium amagasakiense glucose oxidase is essential for the efficient binding of β-D-glucose. Biochem. J. 347, 553-559
40. Guillén, F. (1991) Aril-Alcohol Oxidasa de Pleurotus eryngii. Estudio en Relación con la Degradación de la Lignina, PhD. Thesis, Universidad de Alcalá de Henares, Madrid