Novel Strecker degradation products of tyrosine and dihydroxyphenylalanine
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 a...
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| Format: | Article |
| Language: | English |
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Czech Academy of Agricultural Sciences
2001-02-01
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| Series: | Czech Journal of Food Sciences |
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| Online Access: | https://cjfs.agriculturejournals.cz/artkey/cjf-200101-0003_novel-strecker-degradation-products-of-tyrosine-and-dihydroxyphenylalanine.php |
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| author | J. Adamiec K. Cejpek J. Rössner J. Velíšek |
| author_facet | J. Adamiec K. Cejpek J. Rössner J. Velíšek |
| author_sort | J. Adamiec |
| collection | DOAJ |
| description | 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). |
| first_indexed | 2024-04-10T08:37:10Z |
| format | Article |
| id | doaj.art-8f705954cd9a4d67b95d7bab031a44ea |
| institution | Directory Open Access Journal |
| issn | 1212-1800 1805-9317 |
| language | English |
| last_indexed | 2024-04-10T08:37:10Z |
| publishDate | 2001-02-01 |
| publisher | Czech Academy of Agricultural Sciences |
| record_format | Article |
| series | Czech Journal of Food Sciences |
| spelling | doaj.art-8f705954cd9a4d67b95d7bab031a44ea2023-02-23T03:26:31ZengCzech Academy of Agricultural SciencesCzech Journal of Food Sciences1212-18001805-93172001-02-01191131810.17221/6568-CJFScjf-200101-0003Novel Strecker degradation products of tyrosine and dihydroxyphenylalanineJ. Adamiec0K. Cejpek1J. Rössner2J. Velíšek3Institute of Chemical Technology Department of Food Chemistry and Analysis, Prague, Czech RepublicInstitute of Chemical Technology Department of Food Chemistry and Analysis, Prague, Czech RepublicInstitute of Chemical Technology Department of Food Chemistry and Analysis, Prague, Czech RepublicInstitute of Chemical Technology Department of Food Chemistry and Analysis, Prague, Czech RepublicTyrosine 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).https://cjfs.agriculturejournals.cz/artkey/cjf-200101-0003_novel-strecker-degradation-products-of-tyrosine-and-dihydroxyphenylalanine.phpstrecker degradationamino acidsglyoxalsodium peroxodisulphateradicalstyrosine3,4-dihydroxyphenyl-alanine (dopa)4-hydroxyphenylacetaldehyde, 3,4-dihydroxyphenylacetaldehyde |
| spellingShingle | J. Adamiec K. Cejpek J. Rössner J. Velíšek Novel Strecker degradation products of tyrosine and dihydroxyphenylalanine Czech Journal of Food Sciences strecker degradation amino acids glyoxal sodium peroxodisulphate radicals tyrosine 3,4-dihydroxyphenyl-alanine (dopa) 4-hydroxyphenylacetaldehyde, 3,4-dihydroxyphenylacetaldehyde |
| title | Novel Strecker degradation products of tyrosine and dihydroxyphenylalanine |
| title_full | Novel Strecker degradation products of tyrosine and dihydroxyphenylalanine |
| title_fullStr | Novel Strecker degradation products of tyrosine and dihydroxyphenylalanine |
| title_full_unstemmed | Novel Strecker degradation products of tyrosine and dihydroxyphenylalanine |
| title_short | Novel Strecker degradation products of tyrosine and dihydroxyphenylalanine |
| title_sort | novel strecker degradation products of tyrosine and dihydroxyphenylalanine |
| topic | strecker degradation amino acids glyoxal sodium peroxodisulphate radicals tyrosine 3,4-dihydroxyphenyl-alanine (dopa) 4-hydroxyphenylacetaldehyde, 3,4-dihydroxyphenylacetaldehyde |
| url | https://cjfs.agriculturejournals.cz/artkey/cjf-200101-0003_novel-strecker-degradation-products-of-tyrosine-and-dihydroxyphenylalanine.php |
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