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Impact of the N-terminal amino acid on the formation of pyrazines from peptides in Maillard model systems

Fien Van Lancker UGent, An Adams UGent and Norbert De Kimpe UGent (2012) JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. 60(18). p.4697-4708
abstract
Only a minor part of Maillard reaction studies in literature focused on the reaction between carbohydrates and peptides. Therefore, in continuation of a previous study in which the influence of the peptide C-terminal amino acid was investigated, this study focused on the influence of the peptide N-terminal amino acid on the production of pyrazines in model reactions of glucose, methylglyoxal, or glyoxal. Nine different dipeptides and three tripeptides were selected. It was shown that the structure of the N-terminal amino acid is determinative for the overall pyrazine production. Especially the production of 2,5(6)-dimethylpyrazine and trimethylpyrazine was low in case of proline, valine, or leucine at the N-terminus, while it was very high for glycine, alanine, or serine. In contrast to the alkyl substituted pyrazines, unsubstituted pyrazine was always produced more in case of experiments with free amino acids. It is clear that different mechanisms must be responsible for this observation. This study clearly illustrates the capability of peptides to produce flavor compounds like pyrazines.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
Maillard, peptides, pyrazines, flavor, model reactions, SBSE, THERMAL INTERACTION, GLUTATHIONE, CYSTEINE, GLUCOSE, DEGRADATION, TRIGLYCINE, DIGLYCINE, GLYCINE, LYSINE, WATER
journal title
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
J. Agric. Food Chem.
volume
60
issue
18
pages
4697 - 4708
Web of Science type
Article
Web of Science id
000303696000035
JCR category
AGRICULTURE, MULTIDISCIPLINARY
JCR impact factor
2.906 (2012)
JCR rank
1/56 (2012)
JCR quartile
1 (2012)
ISSN
0021-8561
DOI
10.1021/jf301315b
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
2121923
handle
http://hdl.handle.net/1854/LU-2121923
date created
2012-05-30 13:57:14
date last changed
2012-05-31 09:59:36
@article{2121923,
  abstract     = {Only a minor part of Maillard reaction studies in literature focused on the reaction between carbohydrates and peptides. Therefore, in continuation of a previous study in which the influence of the peptide C-terminal amino acid was investigated, this study focused on the influence of the peptide N-terminal amino acid on the production of pyrazines in model reactions of glucose, methylglyoxal, or glyoxal. Nine different dipeptides and three tripeptides were selected. It was shown that the structure of the N-terminal amino acid is determinative for the overall pyrazine production. Especially the production of 2,5(6)-dimethylpyrazine and trimethylpyrazine was low in case of proline, valine, or leucine at the N-terminus, while it was very high for glycine, alanine, or serine. In contrast to the alkyl substituted pyrazines, unsubstituted pyrazine was always produced more in case of experiments with free amino acids. It is clear that different mechanisms must be responsible for this observation. This study clearly illustrates the capability of peptides to produce flavor compounds like pyrazines.},
  author       = {Van Lancker, Fien and Adams, An and De Kimpe, Norbert},
  issn         = {0021-8561},
  journal      = {JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY},
  keyword      = {Maillard,peptides,pyrazines,flavor,model reactions,SBSE,THERMAL INTERACTION,GLUTATHIONE,CYSTEINE,GLUCOSE,DEGRADATION,TRIGLYCINE,DIGLYCINE,GLYCINE,LYSINE,WATER},
  language     = {eng},
  number       = {18},
  pages        = {4697--4708},
  title        = {Impact of the N-terminal amino acid on the formation of pyrazines from peptides in Maillard model systems},
  url          = {http://dx.doi.org/10.1021/jf301315b},
  volume       = {60},
  year         = {2012},
}

Chicago
Van Lancker, Fien, An Adams, and Norbert De Kimpe. 2012. “Impact of the N-terminal Amino Acid on the Formation of Pyrazines from Peptides in Maillard Model Systems.” Journal of Agricultural and Food Chemistry 60 (18): 4697–4708.
APA
Van Lancker, F., Adams, A., & De Kimpe, N. (2012). Impact of the N-terminal amino acid on the formation of pyrazines from peptides in Maillard model systems. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 60(18), 4697–4708.
Vancouver
1.
Van Lancker F, Adams A, De Kimpe N. Impact of the N-terminal amino acid on the formation of pyrazines from peptides in Maillard model systems. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. 2012;60(18):4697–708.
MLA
Van Lancker, Fien, An Adams, and Norbert De Kimpe. “Impact of the N-terminal Amino Acid on the Formation of Pyrazines from Peptides in Maillard Model Systems.” JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 60.18 (2012): 4697–4708. Print.