High-Resolution Mass Spectrometry Analysis of Melanoidins and Their Precursors Formed in a Model Study of the Maillard Reaction of Methylglyoxal with L-Alanine or L-Lysine

Despite more than 100 years of research, formation of food melanoidins from carbohydrates and amino acids in the course of the Maillard reaction is still not fully understood. Experiments with relevant precursors are commonly used to limit the pathways of the complex reaction and to elucidate the formation mechanisms of the colored end-products. Here as a simple model, methylglyoxal was incubated with L-alanine or L-lysine in aqueous solutions at 100 degrees C and pH S. The reaction mixtures were analyzed for color formation, molecular weight distribution, and conversion of methylglyoxal. High-resolution mass spectrometry was used to characterize the variety of products formed. With the help of Kendrick and van Krevelen analyses, the complex data sets were investigated for common substructures and reaction patterns. This study revealed that methylglyoxal forms oligomers via aldol reaction under involvement of its prevalent reaction products such as formaldehyde, acetaldehyde, acetol, and aminoacetone with amino acids.

Automated summary

Research on the formation of food melanoidins from carbohydrates and amino acids in the Maillard reaction remains incomplete after more than 100 years. By incubating methylglyoxal with amino acids in aqueous solutions, this study revealed the formation of oligomers through aldol reaction involving key reaction products, such as formaldehyde and aminoacetone. High-resolution mass spectrometry and chemical structure analysis were used to characterize the variety of products formed.