Abstract
In the course of a study of possible mechanisms for chemical evolution in the primeval sea, we found the novel formation of α-amino acids and N-acylamino acids from α-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 HCl. 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 α-ketoglutaric acid, phenylpyruvic acid and oxaloacetic acid, respectively, under similar conditions. N-Succinylglutamic acid was obtained as an intermediate in glutamic acid synthesis. Phenylacetylphenyl-alanineamide 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.
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Yanagawa, H., Makino, Y., Sato, K. et al. Novel formation of α-amino acid from α-oxo acids and ammonia in an aqueous medium. Origins Life Evol Biosphere 14, 163–169 (1984). https://doi.org/10.1007/BF00933654
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DOI: https://doi.org/10.1007/BF00933654