Chemical changes in ultra-heat-treated milk during storage: II. Lactuloselysine and fructoselysine formation by the maillard reaction

Summary Lactuloselysine (ε-N-deoxylactulosyl-L-lysine) and fructoselysine (ε-N-deoxyfructosyl-L-lysine), formed by Maillard reaction, were identified in enzymic hydrolysates of casein from stored ultra-heat-treated (UHT) milk. Furosine (ε-N-(2-furoylmethyl-L-lysine) and pyridosine (ε-(3-hydroxy-4-oxo-6-methyl-1-pyridinyl)-L-norleucine) were identified in the corresponding acid hydrolysates. Enzymic hydrolysis of the caseins, gel filtration and preparative scale amino acid analysis were used to isolate the compounds which were then identified by reference to synthesized authentic compounds. Lactuloselysine formation was extensive and involved 10–30% of lysine residues in UHT milks stored at 30–37 °C for 6 months to 3 years. Fructoselysine concentration was generally about 10% of the lactuloselysine concentration.