Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

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

  • 225 Accesses

  • 11 Citations


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.

This is a preview of subscription content, log in to check access.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8


  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

Download references


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

Author information

Correspondence to Jianmeng Chen.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

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

Download citation


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