水溶液中でのα-オキソ酸からのα-アミノ酸の形成

概要

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In the course of experimental studies on chemical evolution in primeval sea, we discovered a novel way for amino acid formation via N-acylamino acid from an aqueous mixture of α-oxo acid and ammonium sulfate. Glycine and alanine were produced from glyoxylate and pyruvate through N-oxalylglycine and N-acetylalanine, respectively. The process was extended to the formation of other amino acids. Serine, glutamic acid, and phenylalanine were produced from hydroxypyruvate, α-ketoglutarate, and phenylpyruvate, respectively, in aqueous medium under similar conditions. In the case of glutamic acid formation, N-succinylglutamic acid, which was partially converted to pyroglutamic acid was found as an intermediate. However, in the case of phenylalanine formation, N-phenylacetylphenylalanineamide (mp 190_??_191°C) was isolated and identified by IR (3170, 1660, 1640, 1530cm-1), NMR [δ (ppm)=7.18 (10 H, s), 4.45 (1 H, m), 3.38 (2 H, s), 3.20_??_2.60 (2 H, m)], MS [282 (M+), 238], and traditional synthesis, as an intermediate, instead of N-phenylacetylphenylalanine. From oxaloacetate in similar conditions, alanine was produced instead of the expected aspartic acid. In these reactions, the decarboxylation processes were essential for yielding N-acylamino acids when employing α-oxo acids except for glyoxylic acid (R-CO-COOH, R_??_H).
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