Novel aliphatic epoxide hydrolase activities from dematiaceous fungi

FEMS Microbiology Letters

Volumn 141, Issue 2-3, 1996, Pages 239-243

  Grogan, Gideon ^a   Roberts, Stanley M ^b   Willetts, Andrew J ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

Biotransformation; Chiral epoxide; Dematiaceous fungi; Epoxide hydrolase

Indexed keywords

CYCLOHEXANE OXIDE; EPOXIDE HYDROLASE; ETHYLENE OXIDE; STYRENE OXIDE;

ARTICLE; BIOTRANSFORMATION; CATALYST; ENZYME ACTIVITY; FUNGUS; HYDROLYSIS; HYPHOMYCETES; NONHUMAN; PRIORITY JOURNAL;

FUNGI; HYPHOMYCETES; ULOCLADIUM ATRUM; ZOPFIELLA;

EID: 0030222084     PISSN: 03781097     EISSN: None     Source Type: Journal    
DOI: 10.1016/0378-1097(96)00228-5     Document Type: Article

References (16)

1. [1] Pedragosa-Moreau, S., Archelas, A. and Furstoss, R. (1993) Microbiological Transformations 28. Enantiocomplementary epoxide hydrolyses as a preparative access to both enantiomers of styrene oxide. J. Org. Chem. 58, 5533-5536.
2. [2] Mischitz, M., Kroutil, W. Wandel, U. and Faber, K. (1995) Asymmetric microbial hydrolysis of epoxides. Tet. Asymm. 6, 1261-1272.
3. [3] For a review of the use of hepatic epoxide hydrolases and upases in organic synthesis, see Faber, K. (1992) in Biotransformations in Organic Synthesis, Springer, Berlin.
4. [4] Hechtberger, P., Wirnsberger, G., Mischitz, M., Klempier, N. and Faber, K. (1993) Asymmetric hydrolysis of epoxides using an immobilised enzyme preparation from Rhodococcus sp. Tet. Asymm. 4, 1161-1164.
5. [5] Nakamura, T., Nagasawa, T., Yu, F., Watanabe, I. and Yamada, H. (1994) Purification and characterisation of two epoxide hydrolases from Corynebacterium sp. strain N-1074. Appl. Environ. Microbiol. 60, 4630-4633.
6. [6] Kollatukudy, P.E. and Brown, L. (1975) Fate of naturally occurring epoxy acids: a soluble epoxide hydrase which catalyses cis-hydration, from Fusarium solani pisi. Arch. Biochem. Biophys. 166, 599-607.
7. 17 juvenile hormone from its racemic alcohol derivative via fungal metabolism. J. Am. Chem. Soc. 96, 5925-5927.
8. [8] Chen, X.J., Archelas, A. and Furstoss, R. (1993) Microbiological transformations 27. The first examples for preparative-scale enantioselective or diastereoselective epoxide hydrolyses using microorganisms. An unequivocal access to all four bisabolol enantiomers. J. Org. Chem. 58, 5528-5532.
9. [9] Holland, H.L., Brown, F.M. and Larsen, B.G. (1994) Biotransformation of organic sulfides. Part 5. Formation of chiral para-alkyl benzyl methyl sulfoxides by Helminthosporium species NRRL 4671. Tet. Asymm. 5, 1241-1248.
10. [10] Carnell, A.J. and Willetts, A.J. (1992). Biotransformations by fungi: Regio-plus stereoselective Baeyer-Villiger oxidations by dematiaceous fungi. Biotechnol. Lett. 14, 17-20.
11. [11] Oikawa, H., Katayama, K., Suzuki, Y. and Ichihara, A. (1995) Enzymatic activity catalysing exo-selective Diels-Alder reaction in solanapyrone biosynthesis. J. Chem. Soc, Chem. Commun. 1321-1322
12. [12] Ellis, M.B. (1971) Dematiaceous Hyphomycetes, Commonwealth Agricultural Bureau, UK.
13. [13] Turner, W.B. and Aldridge, D.C. (1983) Fungal Metabolites II, Academic Press, London.
14. [14] Ota, K. and Hammock, D. (1980) Cytosolic and microsomal epoxide hydrolases: differential properties in mammalian liver. Science 207, 1479-1481.
15. [15] Bellucci, G., Chiappe, C., Marioni, F. and Benetti, M. (1991) Regioselectivity and enantioselectivity of the cytosolic epoxide hydrolase-catalysed hydrolysis of racemic monosubstituted alkyloxiranes. J. Chem. Soc. Perkin Trans. 1, 361-363.
16. [16] Bellucci, G., Chiappe, C., Cordoni, A. and Marioni, F. (1994) Different enantioselectivity and regioselectivity of the cytosolic and microsomal epoxide hydrolase-catalysed hydrolysis of simple phenyl substituted epoxides. Tet. Lett. 35, 4219-4222.