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Epoxide hydrolase-catalyzed resolution of ethyl 3-phenylglycidate using whole cells of Pseudomonas sp.

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Abstract

A Pseudomonas sp. was isolated with enantioselective epoxide hydrolase activity to ethyl 3-phenylglycidate. Cells grown on sucrose and suspended in 10% (v/v) dimethyl formamide as co-solvent produced (2R,3S) ethyl 3-phenylglycidate with 95% ee and 26% yield in 12 h from 0.2% (w/v) of the racemate.

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References

  • Archelas A, Furstoss R (2001) Synthetic applications of epoxide hydrolases. Curr. Opin. Chem. Biol. 5: 112–119.

    Google Scholar 

  • Argentine JA, Anthony JA (1995) Characterization of a salivary gland-specific esterase in the vector mosquito. Aedes aegypti. Insect Biochem. Mol. Biol. 25: 621–630.

    Google Scholar 

  • Botes AL, Litthauer D, van Tonder A, van Dyk MS (1999) Physicochemical properties of the epoxide hydrolase from Rhodosporidium toruloides. Biotechnol. Lett. 21: 1137–1144.

    Google Scholar 

  • Braun B, Klein E (1996) Immobilization of Candida rugosa lipase to nylon fibers using its carbohydrate groups as the chemical link. Biotech. Bioeng. 51: 327–341.

    Google Scholar 

  • Choi WJ, Huh EC, Park HJ, Lee EY, Choi CY (1998) Kinetic resolution for optically active epoxides by microbial enantioselective hydrolysis. Biotechnol. Tech. 12: 225–228.

    Google Scholar 

  • Genet JP, de Andrade MCC, Ratovelomanana-Vidal V (1995) A new enantioselective synthesis of glycidates via dynamic kinetic resolution of racemic 2-chloro-3-keto esters using chiral Ru complexes. Tetrahedron Lett. 56: 2063–2066.

    Google Scholar 

  • Morisseau C, Venturi G, Moussou P, Baratti J (1998) Effect of carbon and nitrogen sources on the production of a highly enantioselective epoxide hydrolase from Aspergillus niger. Biotechnol. Tech. 22: 805–809.

    Google Scholar 

  • Shibatani T, Omori K, Akatsuka H, Kawai E, Matsumae H (2000) Enzymatic resolution of diltiazem intermediate by Serratia marcescens lipase: molecular mechanism of lipase secretion and its industrial application. J. Mol. Catal. B Enzym. 10: 141–149.

    Google Scholar 

  • Steinreiber A, Faber K (2001) Microbial epoxide hydrolases for preparative biotransformations. Curr. Opin. Biotechnol. 12: 552–558.

    Google Scholar 

  • Vorderwulbecke T (1992) Comparison of lipase by different assay. Enzyme Microb. Technol. 14: 63–638.

    Google Scholar 

  • Weijiers CAJM, de Bont JAM (1999) Epoxide hydrolases from yeasts and other sources: versatile tools in biocatalysis. J. Mol. Catal. B Enzym. 6: 199–214.

    Google Scholar 

  • Zheng GJ, Wang JJ, Ren TR, Yang L, Sun WR (2001) Lipase-catalyzed hydrolysis of methyl-3-phenylglycidate. Chin. Chem. Lett. 12: 305–306.

    Google Scholar 

  • Zocher F, Enzelberger MM, Bornscheuer UT, Hauer B, Wohlleben W, Schmid RD (2000) Epoxide hydrolase activity of Streptomyces strains. J. Biotechnol. 77: 287–292.

    Google Scholar 

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Authors and Affiliations

  1. State Key Laboratory of Microbial Technology, Shandong University, Jinan, 250100, P.R. China

    Congfa Li, Qiao Liu, Xin Song, Di Ding & Yinbo Qu

  2. School of Pharmacy, Shandong University, Jinan, 250012, P.R. China

    Aiguo Ji

Authors
  1. Congfa Li
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  2. Qiao Liu
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  3. Xin Song
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  4. Di Ding
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  5. Aiguo Ji
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  6. Yinbo Qu
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Correspondence to Yinbo Qu.

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Li, C., Liu, Q., Song, X. et al. Epoxide hydrolase-catalyzed resolution of ethyl 3-phenylglycidate using whole cells of Pseudomonas sp.. Biotechnology Letters 25, 2113–2116 (2003). https://doi.org/10.1023/B:BILE.0000007078.83362.a0

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  • DOI: https://doi.org/10.1023/B:BILE.0000007078.83362.a0

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