Pyrazine Formation from Amino Acids and Reducing Sugars, a Pathway Other than Strecker Degradation

Because the reaction of acyloins with ammonia generates pyrazines and acyloins are not involved with Strecker degradation, this study uses acetoin (a simple acyloin, from sugar degradation) to react with amino acids to determine whether ammonia is released, leading to the formation of tetramethylpyr...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 1998-04, Vol.46 (4), p.1515-1517
Main Author: Shu, Chi-Kuen
Format: Article
Language:English
Subjects:
ACETOIN
ACYLOINS
ALDEHYDES
ALPHA-AMINOBUTYRIC ACID
AMINO ACIDS
BETA-AMINOBUTYRIC ACID
Biological and medical sciences
CHEMICAL REACTIONS
DEAMINATION
EPSILON-AMINOHEXANOIC ACID
FLAVOUR COMPOUNDS
Food industries
Fundamental and applied biological sciences. Psychology
GABA
GAMMA-AMINOBUTYRIC ACID
General aspects
Miscellaneous
NONPROTEIN AMINO ACIDS
PYRAZINES
QUANTITATIVE ANALYSIS
REACTION PRODUCTS
REDUCING SUGARS
STRECKER ALDEHYDE
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Summary:Because the reaction of acyloins with ammonia generates pyrazines and acyloins are not involved with Strecker degradation, this study uses acetoin (a simple acyloin, from sugar degradation) to react with amino acids to determine whether ammonia is released, leading to the formation of tetramethylpyrazine. The results show that all reactions between α-amino acids and acetoin generate not only tetramethylpyrazine but also the corresponding Strecker aldehydes. However, the reactions between β-, γ-, or ε-amino acid and acetoin generate only tetramethylpyrazine. Quantitative analysis shows that among such reactions, both α- and β-amino acids generate significantly higher amounts of tetramethylpyrazine than γ- and ε-amino acids. On the basis of these data, it is proposed mechanistically that α-amino acids decarbonylate to generate the reactive intermediates, 1-hydroxyamines, deamination of which leads to the formation of the Strecker aldehydes. This study demonstrates that pyrazines and Strecker aldehydes are also formed from α-amino acids and reducing sugar via deamination in addition to their formation via the well-known Strecker degradation. Keywords: Strecker degradation; pyrazine formation; deamination; decarbonylation; acyloin; α-amino acid; β-amino acid; γ-amino acid; ε-amino acid; Strecker aldehyde
ISSN:0021-8561
1520-5118
DOI:10.1021/jf970999i