Unravelling glutathione conjugate catabolism in Saccharomyces cerevisiae: the role of glutathione/dipeptide transporters and vacuolar function in the release of volatile sulfur compounds 3-mercaptohexan-1-ol and 4-mercapto-4-methylpentan-2-one

Cordente, Antonio G.; Capone, Dimitra L.; Curtin, Chris

doi:10.1007/s00253-015-6833-5

Cited by 39 publications

(45 citation statements)

References 78 publications

(116 reference statements)

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“…Furthermore, based on conversion yields, it appeared that Cys-3SH was more easily utilised by yeast in the release of 3SH [23] -a substantially lower conversion efficiency for GSH-3SH has since been shown [24] due to the need for yeast to first convert the GSH precursor to its Cys counterpart. [25] …”

Section: Conversion Of 3sh Precursors During Fermentationstereochemicmentioning

confidence: 99%

Spotlight on Varietal Thiols and Precursors in Grapes and Wines

Jeffery¹

2016

Aust. J. Chem.

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Wine is an amazingly complex natural product that requires dedicated scientists to resolve many of its mysteries. Traditional synthetic organic chemistry and modern analytical techniques are powerful tools at the disposal of wine chemists who tackle the complexities of wine in order to improve scientific understanding and provide practical solutions to industry. Part of this quest for knowledge relates to maintaining or improving wine quality, which underpins consumer acceptance and links to the competitiveness of wineries in a global market. Wine aroma is an important aspect of wine quality and garners much attention from researchers. Grape-derived aroma compounds are one area of particular importance owing to their distinctiveness and ability to impart 'varietal aromas' to wines. Varietal thiols imparting tropical and citrus notes that are characteristic of wines such as Sauvignon Blanc have emerged, along with their grape-derived precursors, as an area of interest over the past two decades. These compounds have also caught our attention and we have made some important contributions to this field, including identifying new precursors, developing novel analytical methods, and conducting studies that provide unique insights into the biochemical transformations occurring in grape berries and juice, and during fermentation.

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Section: Conversion Of 3sh Precursors During Fermentationstereochemicmentioning

confidence: 99%

Spotlight on Varietal Thiols and Precursors in Grapes and Wines

Jeffery¹

2016

Aust. J. Chem.

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“…It has been shown that 4-MMP and 3-MH exist in the grape berry as nonvolatile precursors, mainly as conjugates of glutathione (Glut-4-MMP and Glut-3-MH) and cysteine (Cys-4-MMP and Cys-3-MH) (18,19). Dipeptide conjugates of 3-MH, S-3cysteinyl glycinylhexan-1-ol (Cys-Gly-3-MH), and S-3-␥-glutamyl cysteinylhexan-1-ol (␥-Glu-Cys-3-MH) have also been identified (20)(21)(22). The acetate ester of 3-MH (3-MHA) is not formed from a nonvolatile precursor but results from acetylation of 3-MH by the yeast alcohol acetyltransferase ATF1 (23).…”

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confidence: 99%

“…The acetate ester of 3-MH (3-MHA) is not formed from a nonvolatile precursor but results from acetylation of 3-MH by the yeast alcohol acetyltransferase ATF1 (23). Biotransformation of conjugated precursors into free thiols by yeast involves their uptake through amino acid and glutathione (GSH) transporters in the plasma membrane (21,24,25). Once inside the cytoplasm, Glut-3-MH is cleaved to Cys-Gly-3-MH in the yeast vacuole by action of the ␥-glutamate transpeptidase ECM38, which might also catalyze the formation of Cys-3-MH from the precursor dipeptide ␥-Glu-Cys-3-MH (21,26).…”

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confidence: 99%

“…Biotransformation of conjugated precursors into free thiols by yeast involves their uptake through amino acid and glutathione (GSH) transporters in the plasma membrane (21,24,25). Once inside the cytoplasm, Glut-3-MH is cleaved to Cys-Gly-3-MH in the yeast vacuole by action of the ␥-glutamate transpeptidase ECM38, which might also catalyze the formation of Cys-3-MH from the precursor dipeptide ␥-Glu-Cys-3-MH (21,26). The carboxypeptidase responsible for the cleavage of the dipeptide Cys-Gly-3-MH into Cys-3-MH remains to be identified.…”

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confidence: 99%

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Inactivating Mutations in Irc7p Are Common in Wine Yeasts, Attenuating Carbon-Sulfur β-Lyase Activity and Volatile Sulfur Compound Production

Cordente

Borneman

Bartel

et al. 2019

Appl Environ Microbiol

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During alcoholic fermentation of grape sugars, wine yeasts produce a range of secondary metabolites that play an important role in the aroma profile of wines. In this study, we have explored the ability of a large number of wine yeast strains to modulate wine aroma composition, focusing on the release of the “fruity” thiols 3-mercaptohexan-1-ol (3-MH) and 4-mercapto-4-methylpentan-2-one (4-MMP) from their respective cysteinylated nonvolatile precursors. The role of the yeast geneIRC7in thiol release has been well established, and it has been shown that a 38-bp deletion found in many wine strains cause them to express a truncated version of Irc7p that does not possess cysteine-S-conjugate β-lyase activity. In our data, we find thatIRC7allele length alone does not fully explain the capacity of a strain to release thiols. Screening of a large number of strains coupled with analysis of genomic sequence data allowed us to identify several previously undescribed single-nucleotide polymorphisms (SNPs) inIRC7that, when coupled with allele length, more robustly explain the ability of a particular yeast strain to release thiols from their cysteinylated precursors. We also demonstrate that allelic variation ofIRC7not only affects the release of thiols but modulates the formation of negative volatile sulfur compounds from the amino acid cysteine. The results of this study provide winemakers with an improved understanding of the genetic determinants that affect wine aroma and flavor, which can be used to guide the choice of yeast strains that are fit for purpose.IMPORTANCEVolatile sulfur compounds contribute to wine aromas that may be considered pleasant, such as “tropical,” “passionfruit,” and “guava,” as well as aromas that are considered undesirable, such as “rotten eggs,” “onions,” and “sewer.” During fermentation, wine yeasts release some of these compounds from odorless precursor molecules, a process that is most efficient when performed by yeasts that express active forms of the protein Irc7p. We show that most wine yeasts carry mutations that reduce activity of this protein, affecting the formation of volatile sulfur compounds that impart both pleasant and unpleasant aromas. The results provide winemakers with guidance on the choice of yeasts that can emphasize or deemphasize this particular contribution to wine quality.

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“…In all winery yeast strains GEX1 was detectable, which is suggested to increase the glutathione concentration in wine . However, the exact mechanism of glutathione export and the relative importance of GEX1 is still unclear . In the case of S288c, it was possible to verify our PCR screening to the specific DMGs, because of the findings of Nakao et al .…”

Section: Discussionmentioning

confidence: 97%

Novel diagnostic marker genes differentiateSaccharomyceswith respect to their potential application

et al. 2018

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Marker genes are widely used to differentiate and classify yeast at a species level. Diagnostic marker genes (DMGs) derived from a whole genome comparison allow the differentiation of strains of Saccharomyces cerevisiae according to their potential application. This approach, which has not been previously described, uses the software tool BIAst Diagnostic Gene Finder (BADGE). We compared the genome sequences of 25 brewing yeast strains to predict DMGs for the discrimination of Saccharomyces yeasts according to their brewing style. Two promising DMGs were chosen for PCR screening in order to test the presence of these genes in 83 yeast strains. A first PCR screening of 25 top‐fermenting S. cerevisiae strains, using the DMG‐specific primer pairs for wheat beer marker I (putative AMD2) and wheat beer marker II (GEX1), distinguished yeast strains of the wheat beer style from all other beer styles. The PCR screening of an extended set of 83 yeast strains displayed a more variable distribution of the selected DMGs to different potential applications. Furthermore, 60 out of 83 yeast strains were positive for at least one DMG. The diagnostic marker genes proved to be useful for the differentiation of wheat beer strains (100% positive identification for both genes) to German Alt‐Kölsch and ale yeasts (87.5% negative identification for both genes). © 2018 The Institute of Brewing & Distilling

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Unravelling glutathione conjugate catabolism in Saccharomyces cerevisiae: the role of glutathione/dipeptide transporters and vacuolar function in the release of volatile sulfur compounds 3-mercaptohexan-1-ol and 4-mercapto-4-methylpentan-2-one

Cited by 39 publications

References 78 publications

Spotlight on Varietal Thiols and Precursors in Grapes and Wines

Spotlight on Varietal Thiols and Precursors in Grapes and Wines

Inactivating Mutations in Irc7p Are Common in Wine Yeasts, Attenuating Carbon-Sulfur β-Lyase Activity and Volatile Sulfur Compound Production

Novel diagnostic marker genes differentiateSaccharomyceswith respect to their potential application

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