Novel Formation of α-Amino Acids and Their Derivatives from Oxo Acids and Ammonia in an Aqueous Medium

Abstract

In the course of a study of chemical evolution in 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 α-amino acids and their derivatives. A mechanism for the reactions is proposed.