Novel formation of alpha-amino acids and their derivatives from oxo acids and ammonia in an aqueous medium.
In the course of a study of chemical evolution of the primeval sea, a novel reaction of carbonyl compounds with ammonia was found. Glyoxylic acid reacted with ammonia to afford N-oxalylglycine, which gave glycine in a 3-20% yield after 6 N HCl hydrolysis. Similarly, glyoxylic acid was treated with methylamine to give N-oxalylsarcosine, which afforded sarcosine in a 9-12% yield upon hydrolysis. Pyruvic acid reacted with ammonia to give N-acetylalanine, which gave alanine in a 1-4% yield upon hydrolysis. These reactions provide a novel and facile route to alpha-amino acids and their derivatives. A mechanism for the reactions is proposed.
D000596:Amino Acids / Q000138:chemical synthesis*; D000641:Ammonia; D055598:Chemical Phenomena; D002621:Chemistry; D006038:Glyoxylates
D000596:Amino Acids; D006038:Glyoxylates; D000641:Ammonia; C031150:glyoxylic acid