Intermediate role of α-keto acids in the formation of Strecker aldehydes

• Published in: Food chemistry Vol. 141; no. 2; pp. 1140 - 1146
• Main Authors: Hidalgo, Francisco J., Delgado, Rosa M., Zamora, Rosario
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 15-11-2013; Elsevier
• Subjects: Aldehydes - chemistry; Amino acid degradation; Amino acid formation; Amino Acids - chemistry; Biological and medical sciences; Carbonyl–amine reactions; Flavours; Food toxicology; Hydrogen-Ion Concentration; Keto Acids - chemistry; Maillard Reaction; Medical sciences; Models, Chemical; Strecker aldehydes; Toxicology; α-Keto acids; Amino acid formation; Maillard reaction; Strecker aldehydes; AlaKA; IS; Amino acid degradation; LeuKA; Flavours; IleKA; Carbonyl–amine reactions; α-Keto acids; GlyKA; OHP; CysKA; OVA; PheKA; TyrKA; GluKA; MetKA; ValKA; Degradation; Amine; Aminoacid; Aldehyde; Carbonyl; Carbonyl-amine reactions
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/j.foodchem.2013.03.068

•The conversion of amino acids into Strecker aldehydes by α-keto acids has a low Ea (38.2kJ/mol).•During the reaction α-keto acids are converted into their corresponding amino acids.•Amino acids can be degraded by oxidised lipids in a delayed way through α-keto acids.•Oxidised lipids form α-keto acids and then α-keto acids degrade other amino acids.•These coupled reactions allow the recovery of the amino acid degraded by the lipid.
The ability of α-keto acids to covert amino acids into Strecker aldehydes was investigated in an attempt to both identify new pathways for Strecker degradation, and analyse the role of α-keto acids as intermediate compounds in the formation of Strecker aldehydes by oxidised lipids. The results obtained indicated that phenylalanine was converted into phenylacetaldehyde to a significant extent by all α-keto acids assayed; glyoxylic acid being the most reactive α-keto acid for this reaction. It has been proposed that the reaction occurs by formation of an imine between the keto group of the α-keto acid, and the amino group of the amino acid. This then undergoes an electronic rearrangement with the loss of carbon dioxide to produce a new imine. This final imine is the origin of both the Strecker aldehyde and the amino acid from which the α-keto acid is derived. When glycine was incubated in the presence of 4,5-epoxy-2-decenal, the amino acid was converted into glyoxylic acid, and this α-keto acid was then able to convert phenylalanine into phenylacetaldehyde. All these results suggest that Strecker aldehydes can be produced by amino acid degradation initiated by different reactive carbonyl compounds, included those coming from amino acids and proteins. In addition, α-keto acids may act as intermediates for the Strecker degradation of amino acids by oxidised lipids.