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Stereospecific metabolism of isomeric epoxyoctadecanoic acids in the lactone‐producing yeast Sporidiobolus salmonicolor
Author(s) -
Haffner Thomas,
Tressl Roland
Publication year - 1998
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/s11745-998-0179-9
Subject(s) - chemistry , stereospecificity , metabolism , hydrolysis , lactone , yeast , epoxide hydrolase , stereochemistry , biochemistry , organic chemistry , enzyme , microsome , catalysis
The metabolic course of four isomeric epoxyfatty acids derived from oleic‐, elaidic‐, ( Z )‐, and ( E )‐vaccenic acids in the lactone‐producing yeast, Sporidiobolus salmonicolor , was studied by using the deuterium‐labeled precursors. Dihydroxy‐, hydroxyoxo‐, and hydroxy fatty acids as well as γ‐lactones were identified as metabolic intermediates. Quantitative analysis of the label content and estimation of the enantiomeric composition of the lactones established that, in the first step, the racemic epoxyfatty acids were enantiospecifically hydrolyzed by an epoxide hydrolase. During the subsequent metabolism, the stereochemical orientation of the hydroxy groups of the dihydroxyfatty acids were modified by an oxidation/reduction step.