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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
Evidence of the Possible Interaction between Ultrasound and Thiol Precursors
Tomas Roman1, Loris Tonidandel1, Giorgio Nicolini1
1Fondazione Edmund Mach-Technology Transfer Center, via Edmund Mach 1, 38050 San Michele all'Adige, Italy.
Abstract:
The effect of ultrasound (20 kHz, 153 μm) on the prefermentation extraction mechanisms in Sauvignon Blanc grapes was studied, focusing on 3-mercaptohexan-1-ol (3MH) and 4-mercapto-4-methyl-pentan-2-one (4MMP) precursors linked to glutathione (GSH) and cysteine (Cys). The treatment determined a positive extraction trend between the duration (untreated, 3 and 5 min) and the conductivity or the concentration of catechins and total phenols, significantly differentiated after 5 min. Nevertheless, the concentration of the thiol precursors in grape juice not only remained undifferentiated, but that of 3-S-glutathionyl mercaptohexan-1-ol showed a negative trend with the treatment time applied (168 ± 43, 156 ± 36, and 149 ± 32 μg/L, respectively, for control, 3 and 5 min). The divergence on the effect between families of compounds suggests an interaction between the sonication treatment and thiol precursor molecules. In order to evaluate the possible degradation properly, ultrasound was applied in a model solution spiked with 3MH and 4MMP precursors, reproducing the conditions of grapes. Except for Cys-3MH, the mean concentration (n = 5) for the rest of the precursors was significantly lower in treated samples, predominantly in those linked to glutathione (~-22% and ~18% for GSH-3MH and GSH-4MMP) rather than to cysteine (~-6%~-8% for Cys-3MH and Cys-4MMP). The degradation of precursors was associated with a significant increase of 3MH and 4MMP. The formation of volatile thiols following sonication is interesting from a technological point of view, as they are key aroma compounds of wine and potentially exploitable in the wine industry through specific vinification protocols.
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