Straightforward Synthesis of Deuterated Precursors to Demonstate the Biogenesis of Aromatic Thiols in Wine

Aurélie Rolland (1) , Rémi Schneider (2) , Alain Razungles (3) , Christine Le Guernavé (3) , Florine Cavelier (4)

1 Interloire
2 IFV - Institut Français de la Vigne et du Vin
3 SPO - Sciences Pour l'Oenologie
4 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

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 [2H10] 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.

Mots clés: Glutathione; precursor; grapes; wine

Domaines: Chimie organique

Aurélie Rolland, Rémi Schneider, Alain Razungles, Christine Le Guernavé, Florine Cavelier. Straightforward Synthesis of Deuterated Precursors to Demonstate the Biogenesis of Aromatic Thiols in Wine. Journal of Agricultural and Food Chemistry, 2010, 58 (19), pp.10684-10689. ⟨10.1021/jf101996p⟩. ⟨hal-00545881⟩