Formation of sulfur-containing flavor compounds from [13C]-labeled sugars, cysteine, and methionine.
1994
Tressl R. | Kersten E. | Nittka C. | Rewicki D.
The formation of furans, thiophenes, furanones, thiophenones etc. was investigated in a series of [1(or 6)-13C]-glucose and [1-13C]-arabinose/cysteine and methionine model experiments. The labeled compounds were analyzed by capillary GC/MS and NMR-spectroscopy. From their structures the degradation pathways via different reactive intermediates (e.g. 3-deoxyaldoketose, 1-deoxydiketose) and fragmentations were evaluated. Besides the transformations to flavor compounds via identical labeled precursors, major differences in the flavor compounds result from specific Strecker reaction sequences. Major unlabeled compounds e.g. 3-mercaptopropionic acid from cysteine and 4-methylthiobutyric acid from methionine demonstrate transamination/reduction, and the formation of pyruvate and 2-mercaptopropionic acid from [1-13C]-glucose/cysteine indicates beta-elimination.
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