The degradation of L-threose at Maillard reaction conditions.
L-Threose, a comparatively unstable aldose, is produced from L-ascorbic acid in the presence of oxygen and participates vigorously in Maillard reactions, even at comparatively mild conditions. In the present study, the degradation of L-threose at pH 7.0 alone, in the presence of N-alpha-acetyl-L-lysine, and at pH 2.0 alone at 37 degrees C was investigated by identification of some of the products produced in the reactions by means of GLC and GLC-MS. Among the compounds identified were 3-deoxy-tetros-2-ulose (1), the predicted alkaline rearrangement product derived from 1 (2,4-dihydroxybutyrate, the 4-carbon metasaccharinic acid), as well as glyceraldehyde. Isotopic tracer studies clearly show that the glyceraldehyde is produced by loss of C-1 from the starting L-threose molecule. The presence of N-acetyl lysine in incubation solutions appears to accelerate the production of 1, but the formation of glyceraldehyde appears to be independent of the lysine derivative.
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Department of Biochemistry, University of Missouri, Columbia 65211.
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D002849:Chromatography, Gas; D008401:Gas Chromatography-Mass Spectrometry; D007202:Indicators and Reagents; D007700:Kinetics; D015416:Maillard Reaction; D013780:Tetroses / Q000737:chemistry*
D007202:Indicators and Reagents; D013780:Tetroses; C073321:erythrose