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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

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

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

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

  4. 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

  5. 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

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

  7. 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

  8. 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

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

  10. 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

  11. 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

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

  13. 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

  14. 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

  15. 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

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

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

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

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

  20. 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

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

  22. 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

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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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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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Keywords

  • Bacillus sp. Z018
  • Epoxide hydrolase
  • (R)-3-phenoxy-1,2-propanediol
  • Transformation