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Strecker degradation products of aspartic and glutamic acids and their amides

Author

Listed:
  • J. Rössner

    (Institute of Chemical Technology - Department of Food Chemistry and Analysis, Prague, Czech Republic)

  • J. Velíšek

    (Institute of Chemical Technology - Department of Food Chemistry and Analysis, Prague, Czech Republic)

  • F. Pudil

    (Institute of Chemical Technology - Department of Food Chemistry and Analysis, Prague, Czech Republic)

  • J. Davídek

    (Institute of Chemical Technology - Department of Food Chemistry and Analysis, Prague, Czech Republic)

Abstract

Aspartic and glutamic acids, asparagine and glutamine were oxidised with either potassium peroxodisulphate or glyoxal. Nonvolatile products were derivatised and analysed by GC/FID and GC/MS. Volatile reaction products were isolated and analysed by the same methods. It was found that the degradation reactions of amino acids are complex. Amino acids are principally degraded via the corresponding a-keto acids to Strecker aldehydes (aspartic acid to oxalacetic and 3-oxopropionic acids and glutamic acid to a-ketoglutaric and 4-oxobutyric acids), which are unstable and decomposed by decarboxylation to the corresponding aldehydes. Aspartic acid also eliminates ammonia and yields fumaric acid whereas glutamic acid gives rise to an imine, pyroglutamic acid. A recombination of free radicals leads to dicarboxylic acids (succinic acid from aspartic acid, succinic, glutaric and adipic acids from glutamic acid). The major volatile products (besides the aldehydes) are lower carboxylic acids (acetic acid from aspartic acid and propionic acid acid from glutamic acid) that can at least partly arise by radical reactions. In both quality and quantity terms, a higher amount of degradation products arises by oxidation of amino acids by peroxodisulphate.

Suggested Citation

  • J. Rössner & J. Velíšek & F. Pudil & J. Davídek, 2001. "Strecker degradation products of aspartic and glutamic acids and their amides," Czech Journal of Food Sciences, Czech Academy of Agricultural Sciences, vol. 19(2), pages 41-45.
  • Handle: RePEc:caa:jnlcjf:v:19:y:2001:i:2:id:6573-cjfs
    DOI: 10.17221/6573-CJFS
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    Cited by:

    1. Ondřej Novotný & Karel Cejpek & Jan Velíšek, 2008. "Formation of carboxylic acids during degradation of monosaccharides," Czech Journal of Food Sciences, Czech Academy of Agricultural Sciences, vol. 26(2), pages 113-131.

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