Enantioselective hydrolysis of epichlorohydrin using whole Aspergillus niger ZJB-09173 cells in organic solvents

Journal of Biosciences

Volumn 37, Issue 4, 2012, Pages 695-702

  Jin, Huo Xi ^a   Hu, Zhong Ce ^a   Zheng, Yu Guo ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Enantioselective hydrolysis; Enantioselectivity; Epichlorohydrin; Epoxide hydrolase; Organic solvent

Indexed keywords

CYCLOHEXANE; EPICHLOROHYDRIN; EPOXIDE HYDROLASE; ORGANIC SOLVENT;

CATALYSIS; FUNGUS; HYDROLYSIS; INHIBITION; SOLVENT; SUBSTRATE;

ARTICLE; ASPERGILLUS NIGER; CATALYSIS; CONCENTRATION (PARAMETERS); ENANTIOSELECTIVITY; ENZYME STABILITY; ENZYME SUBSTRATE; HYDROLYSIS; NONHUMAN; RACEMIC MIXTURE;

ASPERGILLUS NIGER; CYCLOHEXANES; EPICHLOROHYDRIN; EPOXIDE HYDROLASES; HYDROLYSIS; KINETICS; SOLVENTS; STEREOISOMERISM;

ASPERGILLUS NIGER;

EID: 84866739521     PISSN: 02505991     EISSN: 09737138     Source Type: Journal    
DOI: 10.1007/s12038-012-9243-1     Document Type: Article

References (31)

1. Archelas A and Furstoss R 2001 Synthetic applications of epoxide hydrolases. Curr. Opin. Chem. Biol. 5 112-119
2. Assis HMS, Bull AT and Hardman DJ 1998 Synthesis of chiral epihalohydrins using haloalcohol dehalogenase A from Arthrobacter erithii H10a. Enzyme Microb. Technol. 22 545-551
3. Baldascini H and Janssen DB 2005 Interfacial inactivation of ep-oxide hydrolase in a two-liquid-phase system. Enzyme Microb. Technol. 36 285-293
4. Blee E and Schuber F 1992 Occurrence of fatty-acid epoxide hydrolases in soybean (glycine-max)-purification and characterization of the soluble form. Biochem. J. 282 711-714
5. Choi WJ, Huh EC, Park HJ, Lee EY and Choi CY 1998 Kinetic resolution for optically active epoxides by microbial enantioselective hydrolysis. Biotechnol. Tech. 12 225-228
6. Choi WJ, Lee EY, Yoon SJ, Yang ST and Choi CY 1999 Biocatalytic production of chiral epichlorohydrin in organic solvents. J. Biosci. Bioeng. 88 339-341
7. Furstoss R, Monfort N and Archelas A 2004 Enzymatic transformations. Part 55: Highly productive epoxide hydrolase catalysed resolution of an azole antifungal key synthon. Tetrahedron. 60 601-605
8. Hechtberger P, Wirnsberger G, Mischitz M, Klempier N and Faber K 1993 Asymmetric hydrolysis of epoxides using an immobilized enzyme preparation from Rhodococcus sp. Tetrahedron-Asymmetr. 4 1161-1164
9. Jacobs MHJ, Vandenwijngaard AJ, Pentenga M and Janssen DB 1991 Characterization of the epoxide hydrolase from an epichlorohydrin-degrading Pseudomonas sp. Eur. J. Biol. Chem. 202 1217-1222
10. Jones PD, Wolf NM, Morisseau C, Whetstone P, Hock B and Hammock BD 2005 Fluorescent substrates for soluble epoxide hydrolase and application to inhibition studies. Anal. Biochem. 343 66-75
11. Karboune S, Archelas A and Baratti J 2006 Properties of epoxide hydrolase from Aspergillus niger for the hydrolytic kinetic resolution of epoxides in pure organic media. Enzyme Microb. Technol. 39 318-324
12. Kasai N, Suzuki T and Furukawa Y 1998 Chiral C3 epoxides and halohydrins: Their preparation and synthetic application. J. Mol. Catal. B Enzym. 4 237-252
13. Kasai N, Tsujimura K, Unoura K and Suzuki T 1992 Isolation of (S)-2,3-dichloro-1-propanol assimilating bacterium, its characterization, and its use in preparation of (R)-2,3-dichloro-1-prop-anol and (S)-epichlorohydrin. J. Ind. Microbiol. 10 37-43
14. Kim GJ and Choi SD 2004 Enantioselective hydrolytic kinetic resolution of epoxides catalyzed by chiral Co(III) salen complexes immobilized in the membrane reactor. Catal. Lett. 92 35-40
15. Kim GJ, Kawthekar RB and Ahn CH 2007 Kinetic resolution of terminal epoxides with phenols promoted by heterometallic Co-Al and Co-Ga salen complexes. Catal. Lett. 115 62-69
16. Kotik M and Kyslik P 2006 Purification and characterisation of a novel enantio selective epoxide hydrolase from Aspergillus niger M200. Biochem. Biophys. Acta. 1760 245-252
17. Larrow JF, Hemberger KE, Jasmin S, Kabir H and Morel P 2003 Commercialization of the hydrolytic kinetic resolution of racemic epoxides: toward the economical large-scale production of enantiopure epichlorohydrin. Tetrahedron-Asymmetr. 14 3589-3592
18. Lee EY 2007 Enantioselective hydrolysis of epichlorohydrin in organic solvents using recombinant epoxide hydrolase. J. Ind. Eng. Chem. 13 159-162
19. Liu Z-Q, Zhang L-P, Cheng F, Ruan L-T, Hu Z-C, Zheng Y-G and Shen Y-C 2011 Characterization of a newly synthesized epoxide hydrolase and its application in racemic resolution of (R, S)-epichlorohydrin. Catal. Commun. 16 133-139
20. Manoj KM, Archelas A, Baratti J and Furstoss R 2001 Microbiological transformations. Part 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. 57 695-701
21. Meijer J and Depierre JW 1988 Cytosolic epoxide hydrolase. Chem-Biol. Interact. 24 207-249
22. Miroliaei M and Nemat-Gorgani M 2002 Effect of organic solvents on stability and activity of two related alcohol dehydrogenases: a comparative study. Int. J. Biochem. Cell Biol. 34 169-175
23. Morisseau C, Archelas A, Guitton C, Faucher D, Furstoss P and Baratti JC 1999 Purification and characterization of a highly enantioselective epoxide hydrolase from Aspergillus niger. Eur. J. Biochem. 263 386-395
24. Morisseau C, Nellaiah H, Archelas A, Furstoss R and Baratti JC 1997 Asymmetric hydrolysis of racemic para-nitrostyrene oxide using an epoxide hydrolase preparation from Aspergillus niger. Enzyme Microb. Technol. 20 446-452
25. Nellaiah H, Morisseau C, Archelas A, Furstoss R and Baratti JC 1996 Enantioselective hydrolysis of p-nitrostyrene oxide by an epoxide hydrolase preparation from Aspergillus niger. Biotechnol. Bioeng. 49 70-77
26. Spelberg JHL, Tang LX, Kellogg RM and Janssen DB 2004 Enzymatic dynamic kinetic resolution of epihalohydrins. Tetrahedron-Asymmetr. 15 1095-1102
27. Spelberg JHL, Tang LX, van Gelder M, Kellogg RM and Janssen DB 2002 Exploration of the biocatalytic potential of a halohy-drin dehalogenase using chromogenic substrates. Tetrahedron-Asymmetry 13 1083-1089
28. Thompson DA and Hammock BD 2007 Dihydroxyoctadecamonoenoate esters inhibit the neutrophil respiratory burst. J. Biosci. 32 279-291
29. Tsitsimpikou C, Voutou D, Christakopoulos P, Kekos D, Macris BJ and Kolisis FN 1994 Studies of the effect of organic-solvents on the stability of beta-glucosidase from fusarium-oxysporum. Biotechnol. Lett. 16 57-62
30. Volkin DB, Staubli A, Langer R and Klibanov AM 1991 Enzyme thermoinactivation in anhydrous organic-solvents. Biotechnol. Bioeng. 37 843-853
31. Woo JH, Hwang YO, Kang JH, Lee HS, Kim SJ and Kang SG 2010 Enantioselective hydrolysis of racemic epichlorohydrin using an epoxide hydrolase from Novosphingobium aromaticivorans. J. Biosci. Bioeng. 110 295-297