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Xanthobacter sp. C20 contains a novel bioconversion pathway for limonene.

M J van der Werf1, P M Keijzer, P H van der Schaft

  • 1Division of Industrial Microbiology, Department of Food Technology and Nutritional Sciences, Wageningen University, Wageningen, The Netherlands. vanderwerf@voeding.tno.nl

Journal of Biotechnology
|November 25, 2000
PubMed
Summary

Xanthobacter sp. C20 biotransforms limonene enantiomers into limonene-8,9-epoxide. This novel bioconversion, mediated by induced Cytochrome P-450, shows stereospecificity and is limited by product inhibition.

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Area of Science:

  • Microbial Biotransformation
  • Biocatalysis
  • Enzyme Engineering

Background:

  • Limonene is a cyclic monoterpene with diverse industrial applications.
  • Biocatalytic routes offer sustainable alternatives for chemical synthesis.
  • Stereoselective biotransformation of limonene remains an area of interest.

Purpose of the Study:

  • To isolate and characterize microorganisms capable of limonene bioconversion.
  • To identify novel bioconversion products of limonene.
  • To investigate the stereochemical outcomes of limonene enantiomer biotransformation.

Main Methods:

  • Isolation of Xanthobacter sp. C20 from river sediment using cyclohexane as a sole carbon source.
  • Bioconversion assays with (4R)- and (4S)-limonene.

Related Experiment Videos

  • Identification of bioconversion products using analytical techniques.
  • Enzyme induction studies, specifically for Cytochrome P-450.

    • Main Results:

    • Xanthobacter sp. C20 quantitatively converted both limonene enantiomers to limonene-8,9-epoxide.
    • (4R)-limonene yielded exclusively (4R,8R)-limonene-8,9-epoxide.
    • (4S)-limonene produced a mixture of (4S,8R)- and (4S,8S)-limonene-8,9-epoxide (78:22 ratio).
    • Cytochrome P-450 activity was induced during growth on cyclohexane, correlating with bioconversion.
    • Optimal bioconversion rate occurred at 12 mM substrate concentration.
    • Product inhibition limited the formation of limonene-8,9-epoxide up to 0.8 g/L.

    Conclusions:

    • Xanthobacter sp. C20 is a novel microbial catalyst for limonene epoxidation.
    • The bacterium produces a previously undescribed bioconversion product, limonene-8,9-epoxide.
    • The biotransformation exhibits enantioselectivity, with distinct stereochemical outcomes for each limonene enantiomer.
    • Cytochrome P-450 plays a crucial role in this limonene epoxidation pathway.
    • Product inhibition is a significant factor affecting the yield of limonene-8,9-epoxide.