Stereoselectivities of microbial epoxide hydrolases

Current Opinion in Chemical Biology

Volumn 3, Issue 1, 1999, Pages 16-21

  Orru, Romano V A ^a   Faber, Kurt ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL ENZYME; EPOXIDE; EPOXIDE HYDROLASE;

ACTINOBACTERIA; ASPERGILLUS; CATALYSIS; DRUG HYDROLYSIS; ENZYME KINETICS; ENZYME SPECIFICITY; HYDROLYSIS; NOCARDIA; RACEMIC MIXTURE; REVIEW; RHODOCOCCUS; RHODOTORULA; STEREOCHEMISTRY;

EID: 0033055661     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(99)80004-0     Document Type: Article

References (30)

1. Oesch F Mammalian epoxide hydrases. Inducible enzymes catalysing the inactivation of carcinogenic and cytotoxic metabolites derived from aromatic olefinic compounds. Xenobiotica. 3:1972;305-340.
2. Lu AYH, Miwa GT Molecular properties and biological functions of microsomal epoxide hydrase. Annu Rev Pharmacol Toxicol. 20:1980;513-531.
3. ••].
4. ••].
5. Verschueren KHG, Seljee F, Rozeboom HJ, Kalk KH, Dijkstra BW Crystallographic analysis of the catalytic mechanism of haloalkane dehalogenase. Nature. 363:1993;693-698.
6. Mischitz M, Mirtl C, Saf R, Faber K Regioselectivity of Rhodococcus NCIMB 11216 epoxide hydrolase: applicability of E-values for description of enantioselectivity depends on substrate structure. Tetrahedron - Asymmetry. 7:1996;2041-2046.
7. Kroutil W, Genzel Y, Pietzsch M, Syldatk C, Faber K Purification and characterization of a highly selective epoxide hydrolase from Nocardia sp. EH1. J Biotechnol. 61:1998;143-150.
8. Jacobs MHJ, Van den Wijngaard AJ, Pentenga M, Janssen DB Characterization of the epoxide hydrolase from an epichlorohydrin-degrading Pseudomonas sp. Eur J Biochem. 202:1991;1217-1222.
9. Nakamura T, Nagasawa T, Yu F, Watanabe I, Yamada H Purification and characterisation of two epoxide hydrolases from Corynebacterium sp. strain N-1074. Appl Environ Microbiol. 60:1994;4630-4633.
10. Mischitz M, Faber K, Willetts A Isolation of a highly enantioselective epoxide hydrolase from Rhodococcus sp. NCIMB 11216. Biotechnol Lett. 17:1995;893-898.
11. Grogan G, Roberts SM, Willetts AJ Novel aliphatic epoxide hydrolase activities from dematiaceous fungi. FEMS Microbiol Lett. 141:1996;239-243.
12. Rink R, Fennema M, Smids M, Dehmel U, Janssen DB Primary structure and catalytic mechanism of the epoxide hydrolase from Agrobacterium radiobacter AD1. J Biol Chem. 272:1997;14650-14657. This paper describes the successful cloning of a bacterial epoxide hydrolase, together with data on its mechanism of catalysis.
13. Chen C-S, Fujimoto Y, Girdaukas G, Sih CJ Quantitative analysis of biochemical kinetic resolutions of enantiomers 1. J Am Chem Soc. 104:1982;7294-7299.
14. Straathof AJJ, Jongejan JA The enantiomeric ratio: origin, determination and prediction. Enz Microb Technol. 21:1997;559-571. An excellent and comprehensive review about the use of the 'Enantiomeric Ratio' for the determination of the enantioselectivity.
15. Botes AL, Steenkamp JA, Letloenyane MZ, van Dyk MS Epoxide hydrolase activity of Chryseomonas luteola for the asymmetric hydrolysis of aliphatic mono-substituted epoxides. Biotechnol Lett. 20:1998;427-430.
16. Orru RVA, Archelas A, Furstoss R, Faber K Epoxide hydrolases and their synthetic applications. Adv Biochem Eng Biotechnol. 63:1998;145-167. In this paper, and references cited therein, the use of microbial epoxide hydrolases in preparative-scale biotransformations is reviewed.
17. Mischitz M, Kroutil W, Wandel U, Faber K Asymmetric microbial hydrolysis of epoxides. Tetrahedron - Asymmetry. 6:1995;1261-1272.
18. Moussou P, Archelas A, Furstoss R Microbiological transformations 40. Use of fungal epoxide hydrolases for the synthesis of enantiopure alkyl epoxides. Tetrahedron. 54:1998;1563-1572.
19. Weijers CAGM Enantioselective hydrolysis of aryl, alicyclic and aliphatic epoxides by Rhodotorula glutinis. Tetrahedron - Asymmetry. 8:1997;639-647. This paper describes the substrate specificity of the epoxide hydrolase activity of a red yeast for the first time.
20. Botes AL, Weijers CAGM, van Dyk MS Biocatalytic resolution of 1,2-epoxyoctane using resting cells of different yeast strains with novel epoxide hydrolase activities. Biotechnol Lett. 20:1998;421-426.
21. Weijers CAGM, Botes AL, van Dyk MS, de Bont JAM Enantioselective hydrolysis of unbranched aliphatic 1,2-epoxides by Rhodotorula glutinis. Tetrahedron - Asymmetry. 9:1998;467-473.
22. Bellucci G, Chiappe C, Cordoni A Enantioconvergent transformation of racemic cis-β-alkyl substituted styrene oxides to (R,R)-threo-diols by microsomal epoxide hydrolase catalysed hydrolysis. Tetrahedron - Asymmetry. 7:1996;197-202.
23. Spelberg JHL, Rink R, Kellogg RM, Janssen DB Enantioselectivity of a recombinant epoxide hydrolase from Agrobacterium radiobacter. Tetrahedron - Asymmetry. 9:1998;459-466. This paper describes the substrate specificity of a cloned bacterial epoxide hydrolase.
24. Grogan G, Rippe C, Willetts A Biohydrolysis of substituted styrene oxides by Beauveria densa CMC 3240. J Mol Catal B. 3:1997;253-257.
25. Pedragosa-Moreau S, Archelas A, Furstoss R Microbiological transformations 32. Use of epoxide hydrolase mediated biohydrolysis as a way to enantiopure epoxides and vicinal diols: application to substituted styrene oxides. Tetrahedron. 52:1996;4593-4606.
26. Bellucci G, Chiappe C, Cordoni A, Ingrosso G Enantioconvergent transformation of racemic cis-dialkyl-substituted epoxides to (R,R)-threo-diols by microsomal epoxide hydrolase catalysed hydrolysis. Tetrahedron Lett. 37:1996;9089-9092.
27. Chiappe C, Cordoni A, Lo Moro G, Palese CD Deracemisation of cis-dialkyl substituted oxides via enantioconvergent hydrolysis catalysed by microsomal epoxide hydrolase. Tetrahedron - Asymmetry. 9:1998;341-350. A study on the enantio-convergent hydrolysis of epoxides using mammalian liver epoxide hydrolase.
28. Kroutil W, Mischitz M, Faber K Deracemisation of (±)-2,3 disubstituted oxiranes via biocatalytic hydrolysis using bacterial epoxide hydrolases: kinetics of an enantioconvergent process. J Chem Soc Perkin Trans. 1:1997;3629-3636. This paper describes the first enantioconvergent hydrolysis of (±)-epoxides by bacterial epoxide hydrolases on a preparative scale, with full analysis of the kinetics.
29. Mischitz M, Faber K Chemoenzymatic synthesis of (2R,5S)- and (2R,5R)-5-(1-hydroxy-1-methylethyl)-2-methyl-2-vinyl-tetrahydrofuran ('linalool oxide'): preparative application of a highly selective bacterial epoxide hydrolase. Synlett. 1996;978-980.
30. Archer IVJ, Leak DJ, Widdowson DA Chemoenzymic resolution and deracemisation of (±)-1-methyl-1,2-epoxycyclohexane: the synthesis of (1S,2S)-1-methylcyclohexane-1,2-diol. Tetrahedron Lett. 37:1996;8819-8822.