Straightforward synthesis of deuterated precursors to demonstrate the biogenesis of aromatic thiols in wine.
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.
Roland
Aurélie
A
Interloire, 12 rue Etienne Pallu, BP 1921, 37019 Tours Cedex 01, France. roland@supagro.inra.fr
Schneider
Rémi
R
Razungles
Alain
A
Le Guernevé
Christine
C
Cavelier
Florine
F
D003903:Deuterium; D005285:Fermentation; D005638:Fruit / Q000737:chemistry; D005978:Glutathione / Q000031:analogs & derivatives* / Q000096:biosynthesis; D009812:Odorants / Q000032:analysis; D013438:Sulfhydryl Compounds / Q000378:metabolism*; D027843:Vitis / Q000737:chemistry; D014920:Wine / Q000032:analysis*
C463489:S-3-(hexan-1-ol)gluathione; D013438:Sulfhydryl Compounds; D003903:Deuterium; D005978:Glutathione