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A novel enantioselective epoxide hydrolase for (R)-phenyl glycidyl ether to generate (R)-3-phenoxy-1,2-propanediol

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Abstract

Bacillus sp. Z018, a novel strain producing epoxide hydrolase, was isolated from soil. The epoxide hydrolase catalyzed the stereospecific hydrolysis of (R)-phenyl glycidyl ether to generate (R)-3-phenoxy-1,2-propanediol. Epoxide hydrolase from Bacillus sp. Z018 was inducible, and (R)-phenyl glycidyl ether was able to act as an inducer. The fermentation conditions for epoxide hydrolase were 35°C, pH 7.5 with glucose and NH4Cl as the best carbon and nitrogen source, respectively. Under optimized conditions, the biotransformation yield of 45.8% and the enantiomeric excess of 96.3% were obtained for the product (R)-3-phenoxy-1,2-propanediol.

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References

  • Archelas, Furstoss R (1997) Synthesis of enantiopure epoxides through biocatalytic approaches. Annu Rev Microbiol 51:491–525

    Article  CAS  Google Scholar 

  • Blée E, Schuber F (1995) Stereocontrolled hydrolysis of the linoleic acid monoepoxide regioisomers catalyzed by soybean epoxide hydrolase. Eur J Biochem 230:229–234

    Article  Google Scholar 

  • Botes AL (1999) Affinity purification and characterization of a yeast epoxide hydrolase. Biotechnol Lett 21:511–517

    Article  CAS  Google Scholar 

  • Choi WJ, Lee EY, Yoon SJ, Yang ST, Choi CY (1999) Biocatalytic production of chiral epichlorohydrin in organic solvents. J Biosci Bioeng 88:339–341

    Article  CAS  Google Scholar 

  • Cleij M, Archelas A, Furstoss R (1998) Microbiological transformations. Part 42: a two-liquid-phase preparative scale process for an epoxide hydrolase catalysed resolution of para-bromo-α-methyl styrene oxide. Occurrence of a surprising enantioselectivity enhancement. Tetrahedron: Asymmetry 9:1839–1842

    Article  CAS  Google Scholar 

  • Dauvrin T, Deslee P (2002) Epoxide hydrolase. US Patent 6,379,938

  • Gong F, Xu J-H (2005) Bio-resolution of a chiral epoxide using whole cells of Bacillus megaterium ECU1001 in a biphasic system. Enzyme Microb Technol 36:252–257

    Article  CAS  Google Scholar 

  • Hellström H, Steinreiber A, Mayer SF, Faber K (2001) Bacterial epoxide hydrolase-catalyzed resolution of a 2,2-disubstituted oxirane: optimization and upscaling. Biotechnol Lett 23:169–173

    Article  Google Scholar 

  • Kotik M, Brichac J, Kyslik P (2005) Novel microbial epoxide hydrolases for biohydrolysis of glycidyl derivatives. J Biotechnol 120:364–375

    Article  CAS  Google Scholar 

  • Kronenburg NAE, Mutter M, Visser H, de Bont JAM, Weijers CAGM (1999) Purification of an epoxide hydrolase from Rhodotorula glutinis. Biotechnol Lett 21:519–524

    Article  CAS  Google Scholar 

  • Kroutil W, Genzel Y, Pietzsch M, Syldatk C, Faber F (1998) Purification and characterization of a highly selective epoxide hydrolase from Nocardia sp. EH1. J Biotechnol 61:143–150

    Article  CAS  Google Scholar 

  • Mischitz M, Kroutil W, Wandel U, Faber K (1995) Asymmetric microbial hydrolysis of epoxides. Tetrahedron: Asymmetry 6:1261–1272

    Article  CAS  Google Scholar 

  • Miura Y, Yutani K, Takesue H, Fujii K (1977) Microbiological process for preparing l-tartaric acid in presence of surfactants. US Patent 4,017,362

  • Morisseau C, Archelas A, Guitton C, Faucher D, Furstoss R, Baratti JC (1999) Purification and characterization of a highly enantioselective epoxide hydrolase from Aspergillus niger. Eur J Biochem 263:386–395

    Article  CAS  Google Scholar 

  • Moussou P, Archelas A, Baratti J, Furstoss R (1998) Microbiological transformations. Part 39: determination of the regioselectivity occurring during oxirane ring opening by epoxide hydrolases: a theoretical analysis and a new method for its determination. Tetrahedron: Asymmetry 9:1539–1547

    Article  CAS  Google Scholar 

  • Smit MS (2004) Fungal epoxide hydrolases: new landmarks in sequence-activity space. Trends Biotechnol 22:123–129

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  • Swaving J, de Bont JAM (1998) Microbial transformation of epoxides. Enzyme Microb Technol 22:19–26

    Article  CAS  Google Scholar 

  • Touhara K, Prestwich GD (1993) Juvenile hormone epoxide hydrolase. J Biol Chem 268:19604–19609

    CAS  PubMed  Google Scholar 

  • Visser H, De Bont JAM, Verdoes JC (1999) Isolation and characterization of the epoxide hydrolase-encoding gene from Xanthophyllomyces dendrorhous. Appl Microbiol Biotechnol 65:5459–5463

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  • Zhiqiang L, Yin L, Lifeng P (2007) Isolation and identification of a novel Rhodococcus sp. ML-0004 producing epoxide hydrolase and optimization of enzyme production. Process Biochem 42:889–894

    Article  Google Scholar 

Download references

Acknowledgments

This work was sponsored by the Natural Science Foundations of Zhejiang Province (302067, Y304091) and the Found of Education of Zhejiang Province (Y504076).

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Authors and Affiliations

  1. College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou, 310032, People’s Republic of China

    Shijin Wu, Jiajia Shen, Xiaoyun Zhou & Jianmeng Chen

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  1. Shijin Wu
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  2. Jiajia Shen
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  3. Xiaoyun Zhou
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  4. Jianmeng Chen
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Correspondence to Jianmeng Chen.

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Wu, S., Shen, J., Zhou, X. et al. A novel enantioselective epoxide hydrolase for (R)-phenyl glycidyl ether to generate (R)-3-phenoxy-1,2-propanediol. Appl Microbiol Biotechnol 76, 1281–1287 (2007). https://doi.org/10.1007/s00253-007-1098-2

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  • DOI: https://doi.org/10.1007/s00253-007-1098-2

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