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https://hdl.handle.net/2440/55375
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Type: | Journal article |
Title: | Synthesis of the Individual Diastereomers of the Cysteine Conjugate of 3-Mercaptohexanol (3-MH) |
Author: | Pardon, K. Graney, S. Capone, D. Swiegers, J. Sefton, M. Elsey, G. |
Citation: | Journal of Agricultural and Food Chemistry, 2008; 56(10):3758-3763 |
Publisher: | Amer Chemical Soc |
Issue Date: | 2008 |
ISSN: | 0021-8561 1520-5118 |
Statement of Responsibility: | 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 |
DOI: | 10.1021/jf8000444 |
Published version: | http://dx.doi.org/10.1021/jf8000444 |
Appears in Collections: | Agriculture, Food and Wine publications Aurora harvest 5 |
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