The degradation of L-threose at Maillard reaction conditions

Article abstract of DOI:10.1016/0008-6215(94)84225-6

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-α-acetyl-L-lysine, and at pH 2.0 alone at 37 deg 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.