Aspergillus epoxide hydrolase

Several reports regarding the directed evolution of enantioselective epoxide hydrolases (EHs) have appeared [23,57-59]. These enzymes constitute important catalysts in synthetic organic chemistry [4,60]. The first two reported studies concern the Aspergillus niger epoxide hydrolase (ANEH) [57,58]. Initial attempts were made to enhance the enantioselectivity of the AN E H -catalyzed hydrolytic kinetic resolution of glycidyl phenyl ether (rac-19). The WT leads to an Evalue of only 4.6 in favor of (S)-20 (see Scheme 2.4) [58]. 

Lewis DF, Lake BG, Bird MG. Molecular modelling of human microsomal epoxide hydrolase (EH) by homology with a fungal (Aspergillus niger) EH crystal structure of 1.8 A resolution structure-activity relationships in epoxides inhibiting EH activity. Toxicol In Vitro 2005 19 517-22. 

J. Zou, B. M. Hallberg, T. Bergfors, F. Oesch, M. Arand S. L. Mowbray, T. A. Jones, Structure of Aspergillus tiiger Epoxide Hydrolase at 1. 8 A Resolution Implications for the Structure and Function of the Mammalian Microsomal Class of Epoxide Hydrolases , Structure 2000, 8, 111 - 122. 

Epoxide is an important intermediate for various bioactive compounds, so the demand for the chiral epoxide is increasing. Epoxide hydrolase can hydrolyze epoxide enantioselectively (Figure 20).21 For example, Aspergillus niger was used for the hydrolysis of carvone epoxide (Figure 20(a)).2 11 In the reaction of styrene oxide, the... 

Fig. 8. CASTing of the epoxide hydrolase from Aspergillus niger (ANEH) based on the X-ray structure of the WT. Left Defined randomization sites A-E Right Top view of tunnel-like binding pocket showing sites A-E (blue) and the catalytically active D192 (red)...

Zha D, Wilensek S, Hermes M, Jaeger K-E, Reetz MT (2001) Complete reversal of enantioselectivity of an enzyme-catalyzed reaction by directed evolution. Chem Commun (Cambridge UK) 2664-2665 Zou JY, Hallberg BM, Bergfors T, Oesch F, Arand M, Mowbray SL, Jones TA (2000) Structure of Aspergillus niger epoxide hydrolase at 1.8 resolution Implications for the structure and function of the mammalian microsomal class of epoxide hydrolases. Structure (London) 8 111-122... 

Epoxide Hydrolase Origin Aspergillus niger Fluka Lab... 

Enantioselective Hydrolysis of Racemic 1- 2, 3 -Dihydro Benzofb]Furan-4 -yl -1,2-Oxirane. Epoxide hydrolase catalyzes the enantioselective hydrolysis of an epoxide to the corresponding enantiomerically enriched diol and unreacted epoxide (22,23). The (5)-epoxide (12) is a key intermediate in the synthesis of a number of prospective drug candidates (24). The enantiospecific hydrolysis of the racemic 1- 2, 3 -dihydro benzo[b]furan-4 -yl -l,2-oxirane (13) to the corresponding (R)-diol (14) and unreacted -epoxide (12) (Fig. 4A) was demonstrated by Goswami et aL (25). Among cultures evaluated, two Aspergillus niger strains (SC 16310, SC 16311)... 

Yildirim, D., Tiikel, S.S., Alptekin, O. and Alagoz, D. (2013) Immobilized Aspergillus niger epoxide hydrolases cost-effective biocatalysts for the preparation of enantiopure styrene oxide, propylene oxide and epichlorohydrin. /. Mol. Catal. B Enzym., 88, 84r-90. 

Karboune, S., Archelas, A., Furstoss, R. and Baratti, J. (2005) Immobilization of epoxide hydrolase from Aspergillus niger onto DEAE-cellulose enzymatic properties and application for the enantioselective resolution of a racemic epoxide. J. Mol. Catal. B Enzym., 32,175-183. 

Karboune, S., Archelas, A. and Baratti, J.C. (2010) Free and immobilized Aspergillus niger epoxide hydrolase-catalyzed hydrolytic kinetic resolution of racemic p-chlorostyrene oxide in a neat organic solvent medium. Process Biochem., 45,210-216. 

Kotik, M. and Kyslik, P. (2006) Purification and characterisation of a novel enantioselective epoxide hydrolase from Aspergillus niger M200. Biochim. Biophys. Acta, 1760,245-252. 

Deregnaucourt, J., Archelas, A., Barbirato, R, Paris, J.-M. and Furstoss, R. (2007) Enzymatic transformations. 63. High-concentration two liquid-liquid phase Aspergillus niger epoxide hydrolase-catalysed resolution application to trifluoromefhyl-substituted aromatic epoxides. Adv. Synth. Catal., 349,1405-1417. 

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