1. ChemInform Abstract: Biosynthesis of δ-Jasmin Lactone (= (Z)-Dec-7-eno-5-lactone) and (Z,Z)-Dodeca-6,9-dieno-4-lactone in the Yeast Sporobolomyces odorus
- Author
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R. Tressl, A. Nordsieck, and Thomas Haffner
- Subjects
chemistry.chemical_classification ,biology ,Chemistry ,Stereochemistry ,Substrate (chemistry) ,General Medicine ,biology.organism_classification ,Yeast ,chemistry.chemical_compound ,Biosynthesis ,Enantiomer ,Sporobolomyces ,Isomerization ,Lactone ,Aroma - Abstract
(all-Z)-(9,10,12,13,15,16-2H6)Octadeca-9,12,15-trienoic acid ( = α-linolenic acid; D6-4) was synthesized to investigate the biochemical formation of linolenic-acid-derived aroma compounds in cultures of the yeast Sporobolomyces odorus, using an established gas chromatographic/mass spectrometric (GC/MS) method. Three compounds were identified as labeled: (Z)-dec-7-eno-5-lactone (δ-jasmin lactone), (Z,Z)-dodeca-6,9-dieno-4-lactone, and (2E,4Z)-hepta-2,4-dienoic acid. Both lactones were biosynthesized mostly under conservation of the initial configuration from their corresponding oxygenated linolenic-acid intermediates. The application of (13S,9Z,11E,15Z)-13-hydroxy(9,10,12,13,15, 16-2H6)octadeca-9,11,15-trienoic acid (D6-7) as a OH-functionalized precursor of δ-jasmin lactone allowed to gain insight into the stereochemical course of the biosynthesis to both enantiomers of this lactone. In this experiment, 88.3% of the metabolized labeled precursor was transformed under retention of the original configuration of the (R)-enantiomer. This investigation is also a contribution to a better understanding of the CC bond isomerization steps which took place during the β-oxidative degradation of the substrate.
- Published
- 2010
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