Novel Strecker degradation products of tyrosine and dihydroxyphenylalanine
Czech Journal of Food Sciences(2018)
摘要
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).
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关键词
novel strecker degradation products,dihydroxyphenylalanine,tyrosine
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