3-mercaptohexyl-acetate and 3-mercaptohexanol

Three varietal thiols are important for the tropical fruit aromas of Sauvignon blanc: 4-mercapto-4-methylpentan-2-one (4MMP), 3-mercaptohexanol (3MH) and its acetylated derivative 3-mercaptohexyl acetate (3MHA). These thiols are produced by yeast during fermentation from precursors in grape juice. Here we identify genes in Saccharomyces cerevisiae that are required for the transport and cleavage of two thiol precursors: cysteine-4MMP and glutathione-3MH. A full-length copy of IRC7 is absolutely required for the cleavage of both precursors in the tested strains; the deleted form of the enzyme found in most yeast strains is incapable of converting these compounds into detectable thiols. By using strains that overexpress full-length IRC7, we further show that the glutathione transporter OPT1 and the transpeptidase CIS2 are also required for conversion of glut-3MH to its varietal thiol. No transporter for cys-4MMP was identified: a strain deleted for all nine known cysteine transport genes was still capable of converting cys-4MMP to its varietal thiol, and was also able to take up cysteine at high concentrations. Based on these results, we conclude that cysteine and glutathione precursors make a relatively minor contribution to 3MH production from most grape juices.

Topics: Acetates; Biological Transport; Carbon-Sulfur Lyases; Cysteine; Dipeptidases; Fermentation; gamma-Glutamyltransferase; Glutathione; Hexanols; Monosaccharide Transport Proteins; Pentanones; Saccharomyces cerevisiae; Saccharomyces cerevisiae Proteins; Sulfhydryl Compounds; Vitis; Wine

The intense tropical fruit aroma of Sauvignon blanc wines has been associated with the varietal thiols 3-mercaptohexanol (3MH), derived from odorless precursors in the grape, and 3-mercaptohexyl acetate (3MHA), arising from 3MH during fermentation. Grapes and juice were sourced from five locations in Marlborough, New Zealand, taking hand-picked grapes and samples at four stages during the mechanical harvesting process and pressing, which were then fermented in replicated 750 mL bottles. With each set of juices, the highest concentrations of Cys-3MH and Glut-3MH were found in the juices pressed to 1 bar, but these juices produced wines with lower 3MH and 3MHA concentrations. With three of the juices, there was an increase in varietal thiol content for wines made from juices that had been machine harvested compared to the hand-picked samples, which matched earlier findings of lower 3MH and 3MHA levels in wines made from hand-picked grapes. Juices that were more oxidized, and which showed a higher absorbance at 420 nm, were found to produce wines with lower 3MH and 3MHA concentrations.

Topics: Acetates; Agriculture; Beverages; Fermentation; Food Handling; Fruit; Hexanols; New Zealand; Odorants; Sulfhydryl Compounds; Vitis; Wine