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|Title:||Synthesis of the Individual Diastereomers of the Cysteine Conjugate of 3-Mercaptohexanol (3-MH)|
|Citation:||Journal of Agricultural and Food Chemistry, 2008; 56(10):3758-3763|
|Publisher:||Amer Chemical Soc|
|Kevin H. Pardon, Sean D. Graney, Dimitra L. Capone, Jan H. Swiegers, Mark A. Sefton and Gordon M. Elsey|
|Abstract:||The individual diastereoisomers of the cysteine conjugate of 3-mercaptohexanol (4) were synthesized with high isomeric purity (>98%). On treatment with Apotryptophanase enzyme, the 3R diastereoisomer of 4 gave an 82% yield of the R enantiomer of 1, with no trace of the 3S enantiomer present. Conversely, the 3S diastereoisomer of 4 gave the 3S enantiomer of 1 (43%) accompanied by a trace of the 3R form (S/R = 98.5:1.5), reflecting the diastereomeric purity of the cysteine conjugate. The same stereochemical outcome was observed when the individual diastereoisomers of 4 were added to fermentations with the Saccharomyces cerevisiae AWRI 1655 yeast strain, which gave 1 in 1% yield. A d(10)-analogue of 1 was synthesized and used as an internal standard to determine, by gas chromatography-mass spectrometry (GC-MS), the amounts of 1 formed in these transformations.|
|Keywords:||Saccharomyces cerevisiae; Hexanols; Sulfhydryl Compounds; Cysteine; Magnetic Resonance Spectroscopy; Fermentation; Stereoisomerism; Gas Chromatography-Mass Spectrometry; Odorants|
|Description:||Copyright © 2008 American Chemical Society|
|Appears in Collections:||Agriculture, Food and Wine publications|
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