Please use this identifier to cite or link to this item: https://hdl.handle.net/2440/64028
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Type: Journal article
Title: Synthesis of wine thiol conjugates and labeled analogues: Fermentation of the glutathione conjugate of 3-mercaptohexan-1-ol yields the corresponding cysteine conjugate and free thiol
Author: Grant-Preece, P.
Pardon, K.
Capone, D.
Cordente, A.
Sefton, M.
Jeffery, D.
Elsey, G.
Citation: Journal of Agricultural and Food Chemistry, 2010; 58(3):1383-1389
Publisher: Amer Chemical Soc
Issue Date: 2010
ISSN: 0021-8561
1520-5118
Statement of
Responsibility: 
Paris A. Grant-Preece, Kevin H. Pardon, Dimitra L. Capone, Antonio G. Cordente, Mark A. Sefton, David W. Jeffery, and Gordon M. Elsey
Abstract: Synthesis of the putative wine thiol precursor 3-S-glutathionylhexan-1-ol (Glut-3-MH) has been undertaken to provide pure reference materials for the development of HPLC-MS/MS methods for precursor quantitation in grape juice and wine, and for use in fermentation experiments. Labeled thiol conjugates were also prepared for use as internal standards. Purification and fermentation of a single diastereomer of Glut-3-MH with VIN13 (CSL1) yielded not only the (R)-enantiomer of the wine impact odorant 3-mercaptohexan-1-ol (3-MH) but also the cysteine conjugate intermediate as a single (R)-diastereomer, as determined by HPLC-MS/MS. Chiral GC-MS was used to quantify the total amount of (R)-3-MH released from the ferments, resulting in a molar conversion yield of the glutathione conjugate of about 3%. Enzymatic degradation of the single (R)-Glut-3-MH diastereomer with a gamma-glutamyltranspeptidase confirmed the stereochemical relationship to the related cysteine conjugate. This is the first demonstration that Glut-3-MH can liberate 3-MH under model fermentation conditions, where the cysteine conjugate is also formed in the process. This furthers our understanding of the nature of wine thiol precursors and opens avenues for additional studies into formation and interchange of wine thiols and their precursors.
Keywords: Synthesis
fermentation
diastereoisomers
wine thiol precursors
varietal thiols
elution order
HPLC-MS/MS
chiral analysis
GC-MS
Rights: Copyright © 2010 American Chemical Society
DOI: 10.1021/jf9037198
Appears in Collections:Agriculture, Food and Wine publications
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