J Agric Food Chem. 2015 Jan 14;63(1):312-8. doi: 10.1021/jf5047317.
The ability of 20 phenolic derivatives to produce the Strecker-type degradation of phenylalanine and phenylglycine methyl ester was studied to investigate both the direct degradation of amino acids and amines by phenolic compounds in the absence of added oxidants and the effect of the number and positions of hydroxyl groups in the aromatic ring of the phenolic compound in relation to its ability to produce carbonyl derivatives from amino compounds. The obtained results showed that polyphenols can produce the Strecker degradation of amino acids and amines in the absence of added oxidants. The only requisite for producing the reaction is the presence of two hydroxyl groups in ortho or para positions. However, the presence of two hydroxyl groups in meta position in an additional aromatic ring can inhibit the Strecker-degrading ability of the hydroxyl groups in ortho or para positions. A reaction pathway that explains all of these findings is proposed. In addition, the effect of reaction conditions on the obtained reaction yields was studied. Activation energies (Ea) for phenylacetaldehyde formation from phenylalanine in the presence of hydroquinone, 1,2,4-trihydroxybenzene, and benzoquinone were 32.9, 31.5, and 28.8 kJ/mol, respectively.
研究了 20 种酚衍生物使苯丙氨酸和苯甘氨酸甲酯发生斯特雷克型降解的能力，以研究在没有添加氧化剂的情况下，酚类化合物对氨基酸和胺的直接降解，以及酚类化合物中芳香环上羟基的数量和位置与其从氨基化合物生成羰基衍生物的能力之间的关系。所得结果表明，多酚可在没有添加氧化剂的情况下产生氨基酸和胺的斯特雷克降解。产生反应的唯一必要条件是邻位或对位存在两个羟基。然而，在另一个芳香环中存在两个处于间位的羟基会抑制邻位或对位羟基的斯特雷克降解能力。提出了一种可以解释所有这些发现的反应途径。此外，还研究了反应条件对获得的反应产率的影响。在对苯二酚、1,2,4-三羟基苯和苯醌存在的情况下，从苯丙氨酸形成苯乙醛的活化能（Ea）分别为 32.9、31.5 和 28.8 kJ/mol。
