Czech J. Food Sci., 2001, 19(1):13-18 | DOI: 10.17221/6568-CJFS
Novel Strecker degradation products of tyrosine and dihydroxyphenylalanine
- Institute of Chemical Technology - Department of Food Chemistry and Analysis, Prague, Czech Republic
Tyrosine was oxidised with either potassium peroxodisulphate or glyoxal. Volatile reaction products were isolated and analysed by GC/FID and GC/MS, derivatised with diazomethane and analysed by the same methods. Eight reaction products were identified. The major products were the expected Strecker aldehyde (4-hydroxyphenylacetaldehyde) and its lower homologue 4-hydroxybenzaldehyde. They were followed by 1-(4-hydroxyphenyl)-3-propionaldehyde, phenylacetaldehyde, benzaldehyde, phenol, 4-hydroxybenzoic, and benzoic acid. Analogously, the oxidation of 3,4-dihydroxyphenylalanine yielded the corresponding Strecker aldehyde (3,4-dihydroxyphenylacetaldehyde), its lower homologue 3,4-dihydroxybenzaldehyde, 3,4-dihydroxybenzoic, 3,4-dihydroxyphenylacetic, and caffeic acid. An identification of these oxidation products of tyrosine and 3,4-dihydroxyphenylalanine assumes homolytic cleavage of the Strecker aldehydes and a recombination of free radicals formed by this cleavage. As minor products, six O- and N-heterocyclic compounds arose in systems containing glyoxal (pyrazine, methyl- and ethylpyrazine, 3-furancarbaldehyde, 5-methyl-2-furancarbaldehyde, 2-pyrrolcarbaldehyde).
Keywords: Strecker degradation; amino acids; glyoxal; sodium peroxodisulphate; radicals; tyrosine; 3,4-dihydroxyphenyl-alanine (DOPA); 4-hydroxyphenylacetaldehyde, 3,4-dihydroxyphenylacetaldehyde
Published: February 28, 2001 Show citation
References
- ADAMIEC J., R�SSNER J., VEL�EK J., CEJPEK K., AVEL J. (2001): Minor Strecker degradation products of phenylalanine and phenylglycine. Eur. Food Res. Technol., 212, 135140. Go to original source...
- B LUMENSTEIN J. J., U KACHUKWU V. C., M OHAN R. S., WHALEN D.L. (1993): Effects of para-substituents on the mechanisms of solvolysis of styrene oxides. J. Org. Chem., 58: 924932. Go to original source...
- BUXTON G.V., MALONE T.N., SALMON G.A. (1997): Oxidation of glyoxal initiated by OH in oxygenated solution. J. Chem. Soc., Faraday Trans., 93: 28892891. Go to original source...
- È ERN� J., È ERN� M., P ALEÈEK M., P ROCH�ZKA M. (1971): Organick� synthesa. Organikum. Academia, Prague: 568569.
- DEGENHARDT T.P., BRINKMANN-FRYE E., BAYNES J.W. (1998): Role of carbonyl stress in aging and age-related diseases. In: OBRIEN J., NURSTEN H.E., CRABBE M.J.C., AMES J.M. (Eds.): The Maillard Reaction in Foods and Medicine. The Royal Society of Chemistry: Cambridge: 310. Go to original source...
- DOOL VAN DEN H., KRATZ P.D. (1963): A generalization of the retention index system including linear temperature programmed gas-liquid partiotion chromatography. J. Chromatogr., 11: 463471. Go to original source... Go to PubMed...
- HOLTZ P., REINHOLD A., CREDNER K. (1939): Enzymic decomposition of L-dihydroxyphenylalanine (DOPA) by liver and intestine. Hoppe-Seylers Z. Physiol. Chem., 261: 278286. Go to original source...
- LANGHELD K. (1909): �ber das Verhalten von α-Aminos�uren genen Natriumhypochlorit. Chem. Ber. Dtsch. Ges., 42: 23602374. Go to original source...
- LIEBICH H.M., FÕRST C. (1985): N-methylation and N,Ndimethylation of amino acids. An artifact production in the analysis of organic acids using diazomethane as derivatizing agent. J. Chromatogr., 338: 3340. Go to original source... Go to PubMed...
- NYKANEN L., SUOMALAINEN H. (1983): Aroma of Beer, Wine and Distilled Alcoholic Beverages. Akademie Verlag, Berlin.
- OGATA Y., KIMURA M., KONDO Y. (1981): Photo-promoted hypochlorite oxidation of α-amino acids. Kinetics and irradiation effect for the Strecker degradation. Bull. Chem. Soc. Jpn. 54: 20572060. Go to original source...
- SCHÕNBERG A., MOUBACHER R. (1952): The Strecker degradation of α-amino acids. Chem. Rev., 50: 261277. Go to original source...
- SCHÕNBERG A., MOUBACHER R., MOSTAFA A. (1948): Degradation of α-amino acids to aldehydes and ketones by interaction with carbonyl compounds. J. Chem. Soc., 176182. Go to original source... Go to PubMed...
- SOLINAS M., CICHELLI A. (1982): Determination of phenolic substances in olive oil by GLC and HPLC; possible role of tyrosol in determination of the quantity of virgin oil in blends with rafined oil. Riv. Soc.Ital. Sci. Aliment., 11: 223230.
- VEL�EK J. (1995): Chemie potravin. OSSIS, T�bor.
This is an open access article distributed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International (CC BY NC 4.0), which permits non-comercial use, distribution, and reproduction in any medium, provided the original publication is properly cited. No use, distribution or reproduction is permitted which does not comply with these terms.