Applied Microbiology and Biotechnology

, Volume 52, Issue 3, pp 380–385 | Cite as

Substrate specificity and stereospecificity of limonene-1,2-epoxide hydrolase from Rhodococcus erythropolis DCL14; an enzyme showing sequential and enantioconvergent substrate conversion

  • M. J. van der Werf
  • R. V. A. Orru
  • K. M. Overkamp
  • H. J. Swarts
  • I. Osprian
  • A. Steinreiber
  • J. A. M. de Bont
  • K. Faber
ORIGINAL PAPER

Abstract

Limonene-1,2-epoxide hydrolase (LEH) from Rhodococcus erythropolis DCL14, an enzyme involved in the limonene degradation pathway of this microlorganism, has a narrow substrate specificity. Of the compounds tested, the natural substrate, limonene-1,2-epoxide, and several alicyclic and 2-methyl-1,2-epoxides (e.g. 1-methylcyclohexene oxide and indene oxide), were substrates for the enzyme. When LEH was incubated with a diastereomeric mixture of limonene-1,2-epoxide, the sequential hydrolysis of first the (1R,2S)- and then the (1S,2R)-isomer was observed. The hydrolysis of (4R)- and (4S)-limonene-1,2-epoxide resulted in, respectively, (1S,2S,4R)- and (1R,2R,4S)-limonene-1,2-diol as the sole product with a diastereomeric excess of over 98%. With all other substrates, LEH showed moderate to low enantioselectivities (E ratios between 34 and 3).

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Copyright information

© Springer-Verlag Berlin Heidelberg 1999

Authors and Affiliations

  • M. J. van der Werf
    • 1
  • R. V. A. Orru
    • 2
  • K. M. Overkamp
    • 1
  • H. J. Swarts
    • 1
  • I. Osprian
    • 2
  • A. Steinreiber
    • 2
  • J. A. M. de Bont
    • 1
  • K. Faber
    • 2
  1. 1.Department of Industrial Microbiology, Department of Food Technology and Nutritional Sciences, P.O. Box 81289, 6700 EV Wageningen University, Wageningen, The Netherlands e-mail: Mariet.vanderWerf@imb.ftns.wau.nl Tel.: +31-317-484412 Fax: +31-317-484978NL
  2. 2.Institute of Organic Chemistry, University of Graz, Graz, AustriaAT

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