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Selective ( R )‐3‐hydroxylation of FA by Stenotrophomonas maltophilia
Author(s) -
Weil Kerstin,
Gruber Patrick,
Heckel Frank,
Harmsen Dag,
Schreier Peter
Publication year - 2002
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-002-0897-z
Subject(s) - stenotrophomonas maltophilia , stenotrophomonas , chemistry , hydroxylation , chromatography , biotransformation , homogentisic acid , linoleic acid , palmitoleic acid , pseudomonas putida , bacteria , biochemistry , stereochemistry , fatty acid , biology , 16s ribosomal rna , gene , enzyme , pseudomonas aeruginosa , genetics
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‐ Z 6‐dodecenoic acid and 3‐hydroxy‐ Z 5, Z 8‐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).