4.7 Article

Straightforward Synthesis of Deuterated Precursors To Demonstrate the Biogenesis of Aromatic Thiols In Wine

Journal

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 58, Issue 19, Pages 10684-10689

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jf101996p

Keywords

Glutathione; precursor; grapes; wine

Funding

  1. Interloire, IFV, (Institut Francais de la Vigne et du Vin)
  2. Sicavac

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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 [H-2(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.

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