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.