title: Identification and quantitation of 3-S-cysteinylglycinehexan-1-ol (Cysgly-3-MH) in Sauvignon blanc grape juice by HPLC-MS/MS.
abstract: Precursors to varietal wine thiols are a key area of grape and wine research. Several such precursors, in the form of odorless conjugates, have been closely studied in recent years. A new conjugate has now been identified as 3-S-cysteinylglycinehexan-1-ol (Cysgly-3-MH), being the dipeptide intermediate between cysteine and glutathione precursors of tropical thiol 3-mercaptohexan-1-ol (3-MH). Authentic Cysgly-3-MH was produced via enzymatic transformation of the glutathione conjugate and used to verify the presence of both diastereomers of Cysgly-3-MH in Sauvignon blanc juice extracts. Cysgly-3-MH was added into our HPLC-MS/MS precursor method, and the validated method was used to quantify this new analyte in a selection of Sauvignon blanc juice extracts. Cysgly-3-MH was found in the highest concentrations (10-28.5 μg/L combined diastereomer total) in extracts from berries that had been machine-harvested and transported for 800 km in 12 h. This dipeptide conjugate was much less abundant than the glutathione and cysteine conjugates in the samples studied. On the basis of the results, the new cysteinylglycine conjugate of 3-MH seemingly has a short existence as an intermediate precursor, which may explain why it has not been identified as a natural juice component until now.
authors.affiliation: The Australian Wine Research Institute, P.O. Box 197, Glen Osmond, South Australia 5064, Australia.
authors.forename: Dimitra L
authors.initials: DL
authors.lastname: Capone
authors.forename: Kevin H
authors.initials: KH
authors.lastname: Pardon
authors.forename: Antonio G
authors.initials: AG
authors.lastname: Cordente
authors.forename: David W
authors.initials: DW
authors.lastname: Jeffery
mesh_terms: D001628:Beverages / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid; D004151:Dipeptides / Q000032:analysis*; D005638:Fruit / Q000737:chemistry*; D000441:Hexanols / Q000032:analysis*; D013438:Sulfhydryl Compounds / Q000737:chemistry; D053719:Tandem Mass Spectrometry; D027843:Vitis
chemical_list: C443379:3-mercaptohexan-1-ol; D004151:Dipeptides; D000441:Hexanols; D013438:Sulfhydryl Compounds