Yanagawa H, Makino Y, Sato K, Nishizawa M, Egami F
Orig Life. 1984;14(1-4):163-9. doi: 10.1007/BF00933654.
In the course of a study of possible mechanisms for chemical evolution in the primeval sea, we found the novel formation of alpha-amino acids and N-acylamino acids from alpha-oxo acids and ammonia in an aqueous medium. Glyoxylic acid reacted with ammonia to form N-oxalylglycine, which gave glycine in a 5-39% yield after hydrolysis with 6N HC1. Pyruvic acid and ammonia reacted to give N-acetylalanine, which formed alanine in a 3-7% overall yield upon hydrolysis. The pH optima in these reactions were between pH 3 and 4. These reactions were further extended to the formation of other amino acids. Glutamic acid, phenylalanine and alanine were formed from alpha-ketoglutaric acid, phenylpyruvic acid and oxaloacetic acid, respectively, under similar conditions. N-Succinylglutamic acid was obtained as an intermediate in glutamic acid synthesis. Phenylacetylphenylalanineamide was also isolated as an intermediate in phenylalanine synthesis. Alanine, rather than aspartic acid, was produced from oxaloacetic acid. These reactions provide a novel route for the prebiotic synthesis of amino acids. A mechanism for the reactions will be proposed.
在对原始海洋中化学进化可能机制的研究过程中，我们发现在水介质中由α-氧代酸和氨可新形成α-氨基酸和N-酰基氨基酸。乙醛酸与氨反应生成N-草酰甘氨酸，用6N盐酸水解后，甘氨酸的产率为5-39%。丙酮酸与氨反应生成N-乙酰丙氨酸，水解后丙氨酸的总产率为3-7%。这些反应的最适pH值在pH 3至4之间。这些反应进一步扩展到其他氨基酸的形成。在类似条件下，分别由α-酮戊二酸、苯丙酮酸和草酰乙酸形成谷氨酸、苯丙氨酸和丙氨酸。N-琥珀酰谷氨酸是谷氨酸合成的中间体。苯乙酰苯丙氨酸酰胺也是苯丙氨酸合成的中间体。由草酰乙酸生成的是丙氨酸，而不是天冬氨酸。这些反应为氨基酸的益生元合成提供了一条新途径。将提出这些反应的机制。
