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Formation of pyrazines in Maillard model systems of lysine-containing dipeptides

Fien Van Lancker (UGent) , An Adams (UGent) and Norbert De Kimpe (UGent)
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Abstract
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.
Keywords
flavor, model reactions, pyrazines, Maillard, Peptides, DIGLYCINE, CYSTEINE, GLYCATION, GLUTATHIONE, GLUCOSE-LYSINE, REACTION-PRODUCTS, THERMAL INTERACTION, RELATIVE REACTIVITIES, AMINO-ACIDS, BAR SORPTIVE EXTRACTION, SBSE

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MLA
Van Lancker, Fien, An Adams, and Norbert De Kimpe. “Formation of Pyrazines in Maillard Model Systems of Lysine-containing Dipeptides.” JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 58.4 (2010): 2470–2478. Print.
APA
Van Lancker, F., Adams, A., & De Kimpe, N. (2010). Formation of pyrazines in Maillard model systems of lysine-containing dipeptides. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 58(4), 2470–2478.
Chicago author-date
Van Lancker, Fien, An Adams, and Norbert De Kimpe. 2010. “Formation of Pyrazines in Maillard Model Systems of Lysine-containing Dipeptides.” Journal of Agricultural and Food Chemistry 58 (4): 2470–2478.
Chicago author-date (all authors)
Van Lancker, Fien, An Adams, and Norbert De Kimpe. 2010. “Formation of Pyrazines in Maillard Model Systems of Lysine-containing Dipeptides.” Journal of Agricultural and Food Chemistry 58 (4): 2470–2478.
Vancouver
1.
Van Lancker F, Adams A, De Kimpe N. Formation of pyrazines in Maillard model systems of lysine-containing dipeptides. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. 2010;58(4):2470–8.
IEEE
[1]
F. Van Lancker, A. Adams, and N. De Kimpe, “Formation of pyrazines in Maillard model systems of lysine-containing dipeptides,” JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 58, no. 4, pp. 2470–2478, 2010.
@article{852403,
  abstract     = {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.},
  author       = {Van Lancker, Fien and Adams, An and De Kimpe, Norbert},
  issn         = {0021-8561},
  journal      = {JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY},
  keywords     = {flavor,model reactions,pyrazines,Maillard,Peptides,DIGLYCINE,CYSTEINE,GLYCATION,GLUTATHIONE,GLUCOSE-LYSINE,REACTION-PRODUCTS,THERMAL INTERACTION,RELATIVE REACTIVITIES,AMINO-ACIDS,BAR SORPTIVE EXTRACTION,SBSE},
  language     = {eng},
  number       = {4},
  pages        = {2470--2478},
  title        = {Formation of pyrazines in Maillard model systems of lysine-containing dipeptides},
  url          = {http://dx.doi.org/10.1021/jf903898t},
  volume       = {58},
  year         = {2010},
}

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