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Selective (R)-3-hydroxylation of FA by Stenotrophomonas maltophilia

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Lipids

Abstract

Soil samples were screened for microorganisms selectively transforming FA. One of the isolated strains was identified as the bacterium Stenotrophomonas maltophilia by its phenotypic features and genotypic characterization by sequencing the ribosomal RNA gene. Using linoleic acid as substrate resulted in the formation of two major compounds. After liquid chromatographic isolation and separation, their structures were elucidated by HPLC-tandem MS, GC-MS, and NMR techniques to be 3-hydroxy-Z6-dodecenoic acid and 3-hydroxy-Z5, Z8-tetradecadienoic acid. In additional experiments, other FA, such as α-linolenic, oleic, palmitoleic, myristoleic, and cis-vaccenic acids, were converted to 3-hydroxylated metabolites of shorter chain lengths as well. Determination of the enantiomeric composition revealed highly enriched (R)-hydroxylation (88–98% enantiomeric excess).

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Abbreviations

CD:

circular dichroism

EMBL:

European Molecular Laboratory Biology Database

ESI:

electrospray ionization

HPLC-MS/MS:

HPLC-tandem mass spectrometry

HRGC:

high-resolution gas chromatography

MDGC:

multidimensional GC

TE:

buffer (Tris+EDTA, pH 7.6)

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Authors and Affiliations

  1. Lehrstuhl für Lebensmittelchemie, Universität Würzburg, Am Hubland, D-97074, Würzburg, Germany

    Kerstin Weil, Patrick Gruber, Frank Heckel & Peter Schreier

  2. Institut für Hygiene und Mikrobiologie, Universität Würzburg, Am Hubland, D-97074, Würzburg, Germany

    Dag Harmsen

Authors
  1. Kerstin Weil
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  2. Patrick Gruber
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  3. Frank Heckel
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  4. Dag Harmsen
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  5. Peter Schreier
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Correspondence to Peter Schreier.

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Weil, K., Gruber, P., Heckel, F. et al. Selective (R)-3-hydroxylation of FA by Stenotrophomonas maltophilia . Lipids 37, 317–323 (2002). https://doi.org/10.1007/s11745-002-0897-z

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  • DOI: https://doi.org/10.1007/s11745-002-0897-z

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