Straightforward synthesis of deuterated precursors to demonstrate the biogenesis of aromatic thiols in wine

J Agric Food Chem. 2010 Oct 13;58(19):10684-9. doi: 10.1021/jf101996p.

Abstract

Straightforward synthesis of labeled S-3-(hexan-1-ol)-glutathione and S-4-(4-methylpentan-2-one)-glutathione has been developed through a conjugate addition optimization study. Sauvignon blanc fermentation experiments with the [(2)H(10)] S-4-(4-methylpentan-2-one)-glutathione used as a tracer released the corresponding deuterated thiol, thus proving the direct relationship with the 4-mercapto-4-methylpentan-2-one under enological conditions. The conversion yield of such transformation was estimated to be close to 0.3%, opening an avenue for additional study on varietal thiol biogenesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Deuterium
  • Fermentation
  • Fruit / chemistry
  • Glutathione / analogs & derivatives*
  • Glutathione / biosynthesis
  • Odorants / analysis
  • Sulfhydryl Compounds / metabolism*
  • Vitis / chemistry
  • Wine / analysis*

Substances

  • S-3-(hexan-1-ol)gluathione
  • Sulfhydryl Compounds
  • Deuterium
  • Glutathione