Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 58, Issue 9, Pages 5685-5691Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf100140h
Keywords
Maillard reaction; 1-deoxyhexo-2,3-diulose; 1-deoxyglucosone; 1-DG; alpha-dicarbonyl compounds; dicarbonyl cleavage; oxidative degradation; tricarbonyl; carboxylic acids
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With this work, we report on further insights into the chemistry of 1-deoxy-o-erythro-hexo-2,3-diulose (1-deoxyglucosone, 1-DG). This alpha-dicarbonyl plays an important role as a highly reactive intermediate in the Maillard chemistry of hexoses. Degradation of 1-DG in the presence of the amino acid L-alanine led to the formation of several products. Lactic acid and glyceric acid were found to be major degradation products. Their formation was dependent on the presence of oxygen. Therefore, a mechanism is postulated based on oxidation leading to a tricarbonyl intermediate. Carbonyl cleavage of this structure should then give rise to carboxylic acids. This mechanism was supported by the isotope distribution observed during degradation of different (13)C-labeled D-glucose isotopomers. Furthermore, we identified 3,5-dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one (gamma-pyranone) to be capable of rehydration forming 1-DG to a minor extent and therefore leading to the same degradation products. The formation of carboxylic acids from gamma-pyranone was also dependent on the presence of oxygen in agreement with the postulated oxidative fragmentation. Finally, we investigated the formation of aldehydes expected as retro-aldol products formed within the degradation of 1-DG. Results seemed to rule out this reaction as an important degradation pathway under the conditions investigated herein.
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