Fungal epoxide hydrolases: New landmarks in sequence-activity space

Trends in Biotechnology

Volumn 22, Issue 3, 2004, Pages 123-129

  Smit, Martha S ^a  

^a UNIVERSITY OF THE FREE STATE   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCATALYSTS; BIOSYNTHESIS; CATALYST ACTIVITY; ESCHERICHIA COLI; FUNGI; GENES; HYDROLYSIS; REACTION KINETICS; YEAST;

GENE SEQUENCES;

ENZYMES;

EPOXIDE; EPOXIDE HYDROLASE; FUNGAL ENZYME; MEMBRANE ENZYME; RECOMBINANT ENZYME;

ENZYME; FUNGUS;

AMINO ACID SEQUENCE; ASPERGILLUS NIGER; BIOCATALYST; CATALYSIS; CATALYST; ENANTIOSELECTIVITY; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME IMMOBILIZATION; ENZYME LOCALIZATION; ENZYME SPECIFICITY; ENZYME STRUCTURE; ENZYME SUBSTRATE; FUNGAL STRAIN; GENE EXPRESSION; GENE SEQUENCE; GENETIC SCREENING; HYDROLYSIS KINETICS; MOLECULAR PHYLOGENY; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN FAMILY; PROTEIN FUNCTION; PROTEIN MOTIF; REVIEW; RHODOTORULA; RHODOTORULA GLUTINIS; SEQUENCE ANALYSIS; SOLUBILITY; WILD TYPE; YEAST;

ASPERGILLUS; ASPERGILLUS NIGER; ESCHERICHIA COLI; FUNGI; RHODOSPORIDIUM; RHODOSPORIDIUM TORULOIDES; RHODOTORULA GLUTINIS;

EID: 1242270555     PISSN: 01677799     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tibtech.2004.01.012     Document Type: Review

References (45)

1. Weijers C.A.G.M., Debont J.A.M. Epoxide hydrolases from yeasts and other sources - versatile tools in biocatalysis. J. Mol. Catal., B Enzym. 6:1999;199-214.
2. Fretland A.J., Omiecinski C.J. Epoxide hydrolases: biochemistry and molecular biology. Chem. Biol. Interact. 129:2000;41-59.
3. Archelas A., Furstoss R. Synthetic applications of epoxide hydrolases. Curr. Opin. Biotechnol. 5:2001;112-119.
4. Arand M., et al. Cloning and molecular characterization of a soluble epoxide hydrolase from Aspergillus-Niger that is related to mammalian microsomal epoxide hydrolase. Biochem. J. 344:1999;273-280.
5. Zou J.Y., et al. Structure of Aspergillus-Niger epoxide hydrolase at 1.8 Ångstrom resolution - implications for the structure and function of the mammalian microsomal class of epoxide hydrolases. Structure. 8:2000;111-122.
6. Monfort N., et al. Enzymatic transformations. Part 53: Epoxide hydrolase-catalysed resolution of key synthons for azole antifungal agents. Tetrahedron Asymmetry. 13:2002;2399-2401.
7. Steinreiber A., Faber K. Microbial epoxide hydrolases for preparative biotransformations. Curr. Opin. Biotechnol. 12:2001;552-558.
8. Botes A.L., et al. Biocatalytic resolution of 1,2-epoxyoctane using novel yeast epoxide hydrolases. Biotechnol. Lett. 20:1998;421-426.
9. Yeates C.A., et al. Biocatalysis of nitro substituted styrene oxide by non-conventional yeasts. Biotechnol. Lett. 25:2003;675-680.
10. Boekhout T. Principles and methods used in yeast classification, and an overview of currently accepted yeast genera. Wolf K. Nonconventional Yeasts in Biotechnology. 1996;1-181 Springer.
11. Botes A.L., et al. Enantioselectivities of yeast epoxide hydrolases for 1,2-epoxides. Tetrahedron Asymmetry. 10:1999;3327-3336.
12. Scorzetti G., et al. Systematics of basidiomycetous yeasts: a comparison of large subuit D1/D2 and internal transcribed spacer rDNA regions. FEM. Yeast Res. 2:2002;495-517.
13. Archelas A., Furstoss R. Epoxide hydrolases - new tools for the synthesis of fine organic-chemicals. Trends Biotechnol. 16:1998;108-116.
14. Moussou P., et al. Clues for the existence of two different epoxide hydrolase activities in the fungus Beauveria bassiana. Enzyme Microb. Technol. 26:2000;414-420.
15. Moussou P., et al. Microbiological transformations 41. Screening for novel fungal epoxide hydrolases. J. Mol. Catal., B Enzym. 5:1998;447-458.
16. Genzel Y., et al. Microbiological transformations 50. Selection of epoxide hydrolases for enzymatic resolution of 2-, 3- or 4-pyridyloxirane. J. Mol. Catal., B Enzym. 16:2002;217-222.
17. Weijers C.A.G.M., et al. Enantioselective hydrolysis of unbranched aliphatic 1,2-epoxides by Rhodotorula-Glutinis. Tetrahedron Asymmetry. 9:1998;467-473.
18. Weijers C.A.G.M. Enantioselective hydrolysis of aryl, alicyclic and aliphatic epoxides by Rhodotorula glutinis. Tetrahedron Asymmetry. 8:1997;639-647.
19. Moussou P., et al. Microbiological transformations 40. Use of fungal epoxide hydrolases for the synthesis of enantiopure alkyl epoxides. Tetrahedron. 54:1998;1563-1572.
20. Moussou P., et al. Microbiological transformations 39. Determination of the regioselectivity occurring during oxirane ring-opening by epoxide hydrolases - a theoretical-analysis and a new method for its determination. Tetrahedron Asymmetry. 9:1998;1539-1547.
21. Morisseau C., et al. Asymmetric hydrolysis of racemic para-nitrostyrene oxide using an epoxide hydrolase preparation from Aspergillus niger. Enzyme Microb. Technol. 20:1997;446-452.
22. Pedragosa-Moreau S., et al. Microbiological transformations 28. Enantiocomplementary epoxide hydrolysis as a preparative access to both enantiomers of styrene oxide. J. Org. Chem. 58:1993;5533-5536.
23. Pedragosa-Moreau S., et al. Microbiological transformations 37. An enantioconvergent synthesis of the -blocker (R)-Nifénalol using a combined chemoenzymatic approach. Tetrahedron. 53:1996;9707-9714.
24. Cleij M., et al. Microbiological transformations 42. A 2-liquid-phase preparative-scale process for an epoxide hydrolase catalyzed resolution of para-bromo-alpha-methyl styrene oxide - occurrence of a surprising enantioselectivity enhancement. Tetrahedron Asymmetry. 9:1998;1839-1842.
25. Manoj K.M., et al. Microbiological transformations 45. A green chemistry preparative scale synthesis of enantiopure building blocks of Eliprodil: elaboration of a high substrate concentration epoxide hydrolase-catalyzed hydrolytic kinetic resolution process. Tetrahedron. 57:2001;695-701.
26. Cagnon J.R., et al. First evaluation of the Brazilian microorganisms biocatalytic potential. Chemosphere. 38:1999;2237-2242.
27. Botes A.L. Affinity purification and characterization of a yeast epoxide hydrolase. Biotechnol. Lett. 21:1999;511-517.
28. Kronenburg N.A.E., et al. Purification of an epoxide hydrolase from Rhodotorula-glutinis. Biotechnol. Lett. 21:1999;519-524.
29. Morisseau C., et al. Purification and characterization of a highly enantioselective epoxide hydrolase from Aspergillus-niger. Eur. J. Biochem. 263:1999;386-395.
30. Kronenburg N.A.E., De Bont J.A.M. Effects of detergents on specific activity and enantioselectivity of the epoxide hydrolase from Rhodotorula glutinins. Enzyme Microb. Technol. 28:2001;210-217.
31. Goswami A., et al. Stereospecific enzymatic hydrolysis of racemic epoxide - a process for making chiral epoxide. Tetrahedron Asymmetry. 10:1999;3167-3175.
32. Choi J.H., et al. Continuous production of enantiopure 1,2-epoxyhexane by yeast epoxide hydrolase in a two-phase membrane bioreactor. Appl. Microbiol. Biotechnol. 54:2000;641-646.
33. Choi W.J., et al. Resolution of 1,2-epoxyhexane by Rhodotorula glutinis using a two-phase membrane bioreactor. Appl. Microbiol. Biotechnol. 53:1999;7-11.
34. Nellaiah H., et al. Enantioselective hydrolysis of p-nitrostyrene oxide by an epoxide hydrolase preparation from Aspergillus niger. Biotechnol. Bioeng. 49:1996;70-77.
35. Krieg H.M., et al. Resolution of 1,2-epoxyoctane by enantioselective catalytic hydrolysis in a membrane bioreactor. J. Membr. Sci. 180:2000;69-80.
36. Krieg H.M., et al. The enantioselective catalytic hydrolysis of racemic 1,2-epoxyoctane in a batch and a continuous process. J. Mol. Catal., B Enzym. 13:2001;37-47.
37. Lye G.J., Woodley J.M. Application of in situ product-removal techniques to biocatalytic processes. Trends Biotechnol. 21:1999;29-37.
38. Visser H., et al. Cloning and characterization of an epoxide hydrolase-encoding gene from Rhodotorula glutinis. Appl. Microbiol. Biotechnol. 53:2000;415-419.
39. Visser H., et al. Cloning, characterization and heterologous expression of epoxide hydrolase-encoding cDNA sequences from yeasts belonging to the genera Rhodotorula and Rhodosporidium. Biotechnol. Lett. 24:2002;1687-1694.
40. Visser H., et al. Isolation and characterization of the epoxide hydrolase-encoding gene from Xanthophyllomyces-dendrorhous. Appl. Environ. Microbiol. 65:1999;5459-5463.
41. Botes A.L., et al. Physico-chemical properties of the epoxide hydrolase from Rhodosporidium toruloides. Biotechnol. Lett. 21:1999;1137-1144.
42. Kazlauskas R.J., Bornscheuer U.T. Biotransformations with lipases. Kelly D.R. Biotechnology 8a - Biotransformations I. 1998;37-191 Wiley-VCH.
43. Faber, K. (1995) Biocatalytic applications. In Biotransformations in Organic Synthesis, Springer-Verlag.
44. Visser H., et al. Construction and characterisation of a genetically engineered Escherichia coli strain for the epoxide hydrolase catalysed kinetic resolution of epoxides. Biocatal. Biotrans. 21:2003;33-40.
45. Chen C.-S., et al. Quantitative analysis of biochemical kinetic resolutions of enantiomers. J. Am. Chem. Soc. 104:1982;7294-7299.