5711-29-5Relevant articles and documents
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Khan
, p. 3018,3021 (1952)
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Biosynthesis of (R)-γ-decanolactone in the yeast Sporobolomyces odorus
Haffner, Thomas,Tressl, Roland
, p. 1218 - 1223 (2007/10/03)
Addition of [9,10-2H2]oleic acid to cultures of the yeast Sporobolomyces odorus led to the formation of labeled (R)-γ-decanolactone and both enantiomers of (Z)-6-γ-dodecenolactone and γ-dodecanolactone. The labeling patterns of these lactones were estimated by a quantitative gas chromatography/mass spectrometry method, suitable for ring-labeled lactones. For the first time, there is strong evidence of oleic acid being a genuine precursor of the important aroma compound (R)-γ-decanolactone. On the basis of the presented and former results, a new biosynthetic pathway of this compound is proposed. Starting with a strict enantioselective (R)-12-hydroxylation of oleic acid as an initial step, the following β-oxidation led to the lactone. In addition, biosynthetic aspects of the formation of (Z)-6-γ-dodecenolactone and γ-dodecanolactone in S. odorus are discussed.