Selective (R)-3-hydroxylation of FA by Stenotrophomonas maltophilia.
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 a-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).
Weil
Kerstin
K
Lehrstuhl für Lebensmittelchemie, Universität Würzburg, Germany.
Gruber
Patrick
P
Heckel
Frank
F
Harmsen
Dag
D
Schreier
Peter
P
D002851:Chromatography, High Pressure Liquid; D005227:Fatty Acids / Q000378:metabolism*; D005838:Genotype; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D010641:Phenotype; D021241:Spectrometry, Mass, Electrospray Ionization; D020615:Stenotrophomonas maltophilia / Q000235:genetics / Q000378:metabolism*
D005227:Fatty Acids