Oxidizing enzymes as biocatalysts

Trends in Biotechnology

Volumn 21, Issue 12, 2003, Pages 543-549

  Burton, Stephanie G ^a  

^a UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMICAL ENGINEERING; OXIDATION;

BIOTRANSFORMATIONS;

ENZYMES;

BACTERIAL ENZYME; CATECHOL OXIDASE; CHLORIDE PEROXIDASE; CYTOCHROME P450; LACCASE; MICROBIAL ENZYME; OXIDOREDUCTASE; OXYGENASE; PEROXIDASE; UNSPECIFIC MONOOXYGENASE;

ENZYME;

ACINETOBACTER; BAEYER VILLIGER REACTION; BIOCATALYST; BIOTRANSFORMATION; CHEMICAL PROCEDURES; CHEMICAL REACTION; DIHYDROXYLATION; ESCHERICHIA COLI; GENETIC ENGINEERING; MOLECULAR DYNAMICS; NONHUMAN; OXIDATION REDUCTION REACTION; POLYMERIZATION; PRIORITY JOURNAL; PSEUDOMONAS; REVIEW; SACCHAROMYCES CEREVISIAE;

ACINETOBACTER; BACTERIA (MICROORGANISMS); ESCHERICHIA COLI; PSEUDOMONAS; SACCHAROMYCES; SACCHAROMYCES CEREVISIAE;

EID: 0242559061     PISSN: 01677799     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tibtech.2003.10.006     Document Type: Review

References (66)

1. Duetz W.A., et al. Using proteins in their natural environment: potential and limitations of microbial whole-cell hydroxylations in applied biocatalysis, 2001. Curr. Opin. Biotechnol. 12:2001;419-425.
2. Boyd D.R., et al. Aromatic dioxygenases: molecular biocatalysis and applications. Curr. Opin. Biotechnol. 12:2001;564-573.
3. Cirino P.C., Arnold F.H. Protein engineering of oxygenases for biocatalysis. Curr. Opin. Chem. Biol. 6:2002;130-135.
4. Holland H.L. C-H activation. Curr. Opin. Chem. Biol. 3:1999;22-27.
5. Schulze B., Wubbolts M.G. Biocatalysis for industrial production of fine chemicals. Curr. Opin. Biotechnol. 10:1999;609-615.
6. Holland H.L. Organic Synthesis with Oxidative Enzymes. 1992;VCH Publishers. pp. 5-40.
7. Silverman R.B. The Organic Chemistry of Enzyme-catalysed Reactions. 2000;Academic Press.
8. Holland H.L., Weber H.K. Enzymatic hydroxylation reactions. Curr. Opin. Biotechnol. 11:2000;547-553.
9. Burton S.G. Laccases and phenol oxidases in organic synthesis - a review. Curr. Org. Chemistry. 7:2003;1-15.
10. Fetzner S. Enzymes involved in aerobic bacterial degradation of N-heteroaromatic compounds: molybdenum hydroxylases and ring-opening 2,4-dioxygenases. Naturwissenschaften. 87:2000;59-69.
11. Wackett L.P. Mechanism and applications of Rieske non-haem iron dioxygenases. Enzyme Microb. Technol. 31:2002;577-587.
12. McGuirl M.A., Dooley D.M. Copper-containing oxidases. Curr. Opin. Chem. Biol. 3:1999;138-144.
13. Van den Heuvel R.H.H., et al. Vanillyl-alcohol oxidase, a tasteful biocatalyst. J. Mol. Catal. B: Enzym. 11:2001;185-188.
14. Smith A.T., Veitch N.C. Substrate binding and catalysis in haem peroxidases. Curr. Opin. Chem. Biol. 2:1998;269-278.
15. Colonna S., et al. Recent biotechnological developments in the use of peroxidases. Trends Biotechnol. 17:1999;163-168.
16. Littlechild J. Haloperoxidases and their role in biotransformation reactions. Curr. Opin. Chem. Biol. 3:1999;28-34.
17. Gelinas P., et al. Oxido-reductases and lipases as dough bleaching agents. Cereal Chem. 75:1998;810-814.
18. Kirk O., et al. Industrial enzyme applications. Curr. Opin. Biotechnol. 13:2002;345-351.
19. Harayama S. Polycyclic aromatic hydrocarbon bioremediation design. Curr. Opin. Biotechnol. 8:1997;268-273.
20. Anderson B.E., et al. Growth of inoculated white rot fungi and their interactions with the bacterial community in soil contaminated with polycyclic aromatic hydrocarbons, as measured by phospholipid fatty acids. Bioresour. Technol. 73:2000;29-36.
21. Singh B.K., Kuhad R.C. Biodegradation of lindane (δ- hexachlorocyclohexane) by the white-rot fungus Trametes hirsutus. Lett. Appl. Microbiol. 28:1999;238-241.
22. terp (CYP108). J. Biol. Chem. 269:1994;28815-28821.
23. Fang J.M., et al. Enzymes in organic synthesis: oxidoreductions. J. Chem. Soc. 1995;967-977.
24. Panke S., et al. Engineering of a stable whole-cell biocatalyst capable of (S)-styrene oxide formation for continuous two-liquid phase applications. Appl. Environ. Microbiol. 65:1999;5619-5623.
25. Sun D.-A., et al. Biotransformation of 4(20),11(12)-taxadiene derivative. Bioorg. Med. Chem. 9:2001;793-800.
26. Holland H.L., et al. Biocatalytic oxidation of S-alkylcysteine derivatives by chloroperoxidase and Beauveria species. J. Mol. Catal., B Enzym. 17:2002;249-256.
27. Bougionkou D.J., Smounou I. Chloroperoxidase-catalysed cyclodimerization of methyl(2E)-2,4-pentadienoate: a [4+2] cycloaddition product. J. Mol. Catal. B Enzym. 17:2002;257-259.
28. Mihovilovic M.D., et al. Baeyer-Villiger oxidations of representative heterocyclic ketones by whole cells of engineered Escherichia coli expressing cyclohexanone monooxygenase. J. Mol. Catal. B Enzym. 11:2001;349-353.
29. Berezina N., et al. Microbial biotransformations. Part 51: The first example of a dynamic kinetic resolution applied to a microbiological Baeyer-Villiger oxidation. Tetrahedron Asymmetry. 13:2002;1953-1955.
30. Alphand V., et al. Towards large-scale synthetic applications of Baeyer-Villiger monooxygenases. Trends Biotechnol. 21:2003;318-323.
31. Buhler B., et al. Characterization and application of xylene monooxygenase for multistep biocatalysis. Appl. Environ. Microbiol. 68:2002;560-568.
32. Suske W.A., et al. Purification and characterization of 2-hydroxybiphenyl 3-monooxygenase, a novel NADH-dependent, FAD-containing aromatic hydroxylase from Pseudomonas azelaica HBP1. J. Biol. Chem. 272:1997;24257-24265.
33. Deluca M.E., Hudlicky T. Microbial oxidation of naphthalene derivatives. Absolute configuration of metabolites. Tetrahedron Lett. 31:1990;13-16.
34. Hagedorn S., Kapehammer B. Microbial biocatalysis in the generation of flavor and fragrance chemicals. Annu. Rev. Microbiol. 48:1994;773-800.
35. Boshoff A., et al. Optimization of catechol production using membrane-immobilised polyphenol oxidase. Biotechnol. Bioeng. 83:2003;1-7.
36. Shao L., et al. Enzymatic modification of the synthetic polymer polyhydroxystyrene. Enzyme Microb. Technol. 25:1999;660-668.
37. Ridgeway T., et al. Novel bioconversions for the production of designer antioxidant and colorant flavanoids using polyphenol oxidases. Biotechnol. Genet. Eng. Rev. 14:1997;165-190.
38. Osiadacz J., et al. On the use of Trametes versicolor laccase for the conversion of 4-methyl-3-hydroxyanthranilic acid to actinocin chromophore. J. Biotechnol. 72:1999;141-149.
39. Uyama H., Kobayashi S. Enzyme-catalysed polymerization to functional polymers. J. Mol. Catal. B Enzym. 785:2002;1-11.
40. Aktas N., Tanyolac A. Kinetics of laccase-catalysed oxidative polymerization of catechol. J. Mol. Catal. B Enzym. 22:2003;61-69.
41. Mikolash A., et al. Synthesis of 3-(3,4-dihyroxyphenyl)-propionic acid derivatives by N-coupling of amines using laccase. Tetrahedron. 38:2002;7589-7593.
42. Giffhorn F., et al. Rare sugars and sugar-base synthons by chemo-enzymatic synthesis. Enzyme Microb. Technol. 27:2000;734-742.
43. Rodakiewicz-Nowak J., et al. Effect of various water miscible solvents on enzymatic activity of fungal laccases. J. Mol. Catal., B Enzym. 11:2000;1-11.
44. Adam W., et al. Biotransformation of (1-phenyl)ethyl hydroperoxide with Aspergillus niger: a model study on enzyme selectivity and on the induction of peroxidase activity. Biochim. Biophys. Acta. 1427:1999;236-244.
45. Van de Velde F., et al. Improving the catalytic performance of peroxidases in organic synthesis. Trends Biotechnol. 19:2001;73-80.
46. Russ R., et al. Benzylic biooxidation of various toluenes to aldehydes by peroxidase. Tetrahedron Lett. 43:2002;791-793.
47. McEldoon J.P., et al. Lignin peroxidase-type activity of soybean peroxidase. Enzyme Microb. Technol. 17:1995;359-365.
48. Lim C.H., Yoo Y.J. Synthesis of ortho-directed polyaniline using horseradish peroxidase. Process Biochem. 36:2000;233-241.
49. Sanfilipino C., Nicolosi G. Catalytic behaviour of chloroperoxidase from Caldariomyces fumago in oxidation of cyclic conjugated dienes. Tetrahedron Asymmetry. 13:2002;1889-1892.
50. Almeida M., et al. Vanadium haloperoxidases from brown algae of the Laninariaceae family. Phytochemistry. 57:2001;633-642.
51. Huisman G.W., Gray D. Towards novel processses for the fine-chemical and pharmaceutical industries. Curr. Opin. Biotechnol. 13:2002;352-358.
52. De Fellipe F.L., et al. Cofactor engineering: a novel approach to metabolic engineering in Lactococcusc lactis by controlled expression of NADH oxidase. J. Bacteriol. 180:1998;3804-3808.
53. Joo H., et al. Laboratory evolution of peroxide-mediated cytochrome P450 hydroxylation. Nature. 399:1999;670-673.
54. Conesa A., et al. Fungal peroxidases: molecular aspects and applications. J. Biotechnol. 93:2002;143-158.
55. Okazaki S., et al. Oxidation of bisphenol A catalysed by laccase hosted in reverse micelles in organic media. Enzyme Microb. Technol. 31:2002;227-232.
56. Gorjup B., et al. Solvent effects on ligninases. Enzyme Microb. Technol. 25:1999;5-22.
57. Guo Y., Clark D.S. Activation of enzymes for non-aqueous biocatalysis by denaturing concentrations of urea. Biochim. Biophys. Acta. 1546:2001;406-411.
58. Morgan J.A., et al. toward the development of a biocatalytic system for oxidation of p-xylene to terephthalic acid: oxidation of 1,4-benzenedimethanol. J. Mol. Catal. B Enzym. 18:2002;147-154.
59. Onda M., et al. Sequential actions of glucose oxidase and peroxidase in molecular films assembled by layer-by-layer alternate adsorption. Biotechnol. Bioeng. 51:1996;163-167.
60. Di Gennaro P., et al. Development of biocatalysts carrying naphthalene dioxygenase and dihydrodiol dehydrogenase genes inducible in aerobic and anaerobic conditions. Res. Microbiol. 151:2000;383-391.
61. Duran N., et al. Applications of laccases and tyrosinases (phenoloxidases) immobilized on different supports: a review. Enzyme Microb. Technol. 31:2002;907-931.
62. Morpurgo M., et al. Covalent modification of mushroom tyrosinase with different amphiphic polymers for pharmaceutical and biocatalysis applications. Appl. Biochem. Biotechnol. 56:1996;58-72.
63. Lin C.-C., Yang M.-C. Cholesterol oxidation using hollow fiber dialiyser immobilised with cholesterol oxidase: preparation and properties. Biotechnol. Prog. 19:2003;361-364.
64. Betancor L., et al. Use of physicochemical tools to determine the choice of optimal enzyme: stabilization of D-amino acid oxidase. Biotechnol. Prog. 19:2003;784-788.
65. Schmid A., et al. The use of enzymes in the chemical industry in Europe. Curr. Opin. Biotechnol. 13:2002;359-366.
66. Burton S.G., et al. The search for the ideal biocatalyst. Nat. Biotechnol. 20:2002;37-45.