TY - JOUR
T1 - Copper(II)-mediated hydrogen sulfide and thiol oxidation to disulfides and organic polysulfanes and their reductive cleavage in wine
T2 - Mechanistic elucidation and potential applications
AU - Kreitman, Gal Y.
AU - Danilewicz, John C.
AU - Jeffery, Davi D.W.
AU - Elias, Ryan J.
N1 - Funding Information:
*(R.J.E.) Phone: (814) 865-5371. Fax: (814) 863-6132. E-mail: [email protected]. ORCID David. W. Jeffery: 0000-0002-7054-0374 Ryan J. Elias: 0000-0001-8416-8772 Present Address ⊥Mondelez̅ International, Inc., 100 Deforest Avenue, East Hanover, NJ 07936, United States. Funding This work was supported in part by a grant (to R.E.) from the Pennsylvania Department of Agriculture and the Pennsylvania Wine Marketing and Research Board. Notes ⊗Retired. The authors declare no competing financial interest.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/3/29
Y1 - 2017/3/29
N2 - Fermentation-derived volatile sulfur compounds (VSCs) are undesirable in wine and are often remediated in a process known as copper fining. In the present study, the addition of Cu(II) to model and real wine systems containing hydrogen sulfide (H2S) and thiols provided evidence for the generation of disulfides (disulfanes) and organic polysulfanes. Cu(II) fining of a white wine spiked with glutathione, H2S, and methanethiol (MeSH) resulted in the generation of MeSH-glutathione disulfide and trisulfane. In the present study, the mechanisms underlying the interaction of H2S and thiols with Cu(II) is discussed, and a prospective diagnostic test for releasing volatile sulfur compounds from their nonvolatile forms in wine is investigated. This test utilized a combination of reducing agents, metal chelators, and low-oxygen conditions to promote the release of H2S and MeSH, at levels above their reported sensory thresholds, from red and white wines that were otherwise free of sulfidic off-odors at the time of addition.
AB - Fermentation-derived volatile sulfur compounds (VSCs) are undesirable in wine and are often remediated in a process known as copper fining. In the present study, the addition of Cu(II) to model and real wine systems containing hydrogen sulfide (H2S) and thiols provided evidence for the generation of disulfides (disulfanes) and organic polysulfanes. Cu(II) fining of a white wine spiked with glutathione, H2S, and methanethiol (MeSH) resulted in the generation of MeSH-glutathione disulfide and trisulfane. In the present study, the mechanisms underlying the interaction of H2S and thiols with Cu(II) is discussed, and a prospective diagnostic test for releasing volatile sulfur compounds from their nonvolatile forms in wine is investigated. This test utilized a combination of reducing agents, metal chelators, and low-oxygen conditions to promote the release of H2S and MeSH, at levels above their reported sensory thresholds, from red and white wines that were otherwise free of sulfidic off-odors at the time of addition.
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U2 - 10.1021/acs.jafc.6b05418
DO - 10.1021/acs.jafc.6b05418
M3 - Article
C2 - 28260381
AN - SCOPUS:85021859896
SN - 0021-8561
VL - 65
SP - 2564
EP - 2571
JO - Journal of agricultural and food chemistry
JF - Journal of agricultural and food chemistry
IS - 12
ER -