Formation of pyrazines in Maillard model systems of lysine-containing dipeptides.
Whereas most studies concerning the Maillard reaction have focused on free amino acids, little information is available on the impact of peptides and proteins on this important reaction in food chemistry. Therefore, the formation of flavor compounds from the model reactions of glucose, methylglyoxal, or glyoxal with eight dipeptides with lysine at the N-terminus was studied in comparison with the corresponding free amino acids by means of stir bar sorptive extraction (SBSE) followed by GC-MS analysis. The reaction mixtures of the dipeptides containing glucose, methylglyoxal, and glyoxal produced 27, 18, and 2 different pyrazines, respectively. Generally, the pyrazines were produced more in the case of dipeptides as compared to free amino acids. For reactions with glucose and methylglyoxal, this difference was mainly caused by the large amounts of 2,5(6)-dimethylpyrazine and trimethylpyrazine produced from the reactions with dipeptides. For reactions with glyoxal, the difference in pyrazine production was rather small and mostly unsubstituted pyrazine was formed. A reaction mechanism for pyrazine formation from dipeptides was proposed and evaluated. This study clearly illustrates the capability of peptides to produce flavor compounds that can differ from those obtained from the corresponding reactions with free amino acids.
Van Lancker
Fien
F
Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium.
Adams
An
A
De Kimpe
Norbert
N
D003553:Cystine / Q000032:analysis; D004151:Dipeptides / Q000737:chemistry*; D005504:Food Analysis; D008401:Gas Chromatography-Mass Spectrometry; D005947:Glucose / Q000032:analysis; D007930:Leucine / Q000032:analysis; D008239:Lysine / Q000032:analysis*; D015416:Maillard Reaction; D010455:Peptides / Q000737:chemistry; D010649:Phenylalanine / Q000032:analysis; D011719:Pyrazines / Q000032:analysis*; D012694:Serine / Q000032:analysis
D004151:Dipeptides; D010455:Peptides; D011719:Pyrazines; D012694:Serine; D010649:Phenylalanine; D003553:Cystine; D007930:Leucine; D005947:Glucose; D008239:Lysine