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https://hdl.handle.net/2440/55375
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dc.contributor.author | Pardon, K. | - |
dc.contributor.author | Graney, S. | - |
dc.contributor.author | Capone, D. | - |
dc.contributor.author | Swiegers, J. | - |
dc.contributor.author | Sefton, M. | - |
dc.contributor.author | Elsey, G. | - |
dc.date.issued | 2008 | - |
dc.identifier.citation | Journal of Agricultural and Food Chemistry, 2008; 56(10):3758-3763 | - |
dc.identifier.issn | 0021-8561 | - |
dc.identifier.issn | 1520-5118 | - |
dc.identifier.uri | http://hdl.handle.net/2440/55375 | - |
dc.description | Copyright © 2008 American Chemical Society | - |
dc.description.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. | - |
dc.description.statementofresponsibility | Kevin H. Pardon, Sean D. Graney, Dimitra L. Capone, Jan H. Swiegers, Mark A. Sefton and Gordon M. Elsey | - |
dc.language.iso | en | - |
dc.publisher | Amer Chemical Soc | - |
dc.source.uri | http://dx.doi.org/10.1021/jf8000444 | - |
dc.subject | Saccharomyces cerevisiae | - |
dc.subject | Hexanols | - |
dc.subject | Sulfhydryl Compounds | - |
dc.subject | Cysteine | - |
dc.subject | Magnetic Resonance Spectroscopy | - |
dc.subject | Fermentation | - |
dc.subject | Stereoisomerism | - |
dc.subject | Gas Chromatography-Mass Spectrometry | - |
dc.subject | Odorants | - |
dc.title | Synthesis of the Individual Diastereomers of the Cysteine Conjugate of 3-Mercaptohexanol (3-MH) | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1021/jf8000444 | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Capone, D. [0000-0003-4424-0746] | - |
Appears in Collections: | Agriculture, Food and Wine publications Aurora harvest 5 |
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