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Current Microbiology

, Volume 71, Issue 1, pp 83–94 | Cite as

Enantioselective Microbial Hydroxylation as a Useful Tool in the Production of Jasmonate Derivatives with Aphid Deterrent Activity

  • Anna Gliszczyńska
  • Witold Gładkowski
  • Katarzyna Dancewicz
  • Beata Gabryś
Article

Abstract

Microbial transformations of two natural compounds dihydrojasmone (1) and cis-jasmone (3) in the growing cultures of selected twenty strains have been investigated. The studies have demonstrated a biocatalytic potential of tested microorganisms for the enantioselective hydroxylation of jasmonates. The substrates underwent an effective regio- and stero-selective hydroxylation at the allylic position in the cyclopentenone ring, and the corresponding optically pure keto-alcohols (2, 4) were obtained. The process of biohydroxylation depended on the composition of reaction medium. In the studied cultures, (+)-(R)-4-hydroxydihydrojasmone (2) and (+) and (−)-4-hydroxyjasmone (4a, 4b) were produced in good yields and high enantiomeric excesses. Moreover, the introduction of the hydroxy group into the molecule of jasmonate ketones 1 and 3 leads to biologically active derivatives 2 and 4 that regulate the behaviour of aphids Myzus persicae by termination of their feeding.

Keywords

Biotransformation Microbial Transformation Pyrethrin Preparative Scale Hydroxyketone 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Notes

Acknowledgments

This Project was financed by the European Union from the European Regional Development Found Grant No. POIG.01.03.01-00-158/09-03.

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Anna Gliszczyńska
    • 1
  • Witold Gładkowski
    • 1
  • Katarzyna Dancewicz
    • 2
  • Beata Gabryś
    • 2
  1. 1.Department of ChemistryWrocław University of Environmental and Life SciencesWrocławPoland
  2. 2.Department of Biology and EcologyUniversity of Zielona GóraZielona GóraPoland

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