Novel formation of alpha-amino acids and their derivatives from oxo acids and ammonia in an aqueous medium

J Biochem. 1982 Jun;91(6):2087-90. doi: 10.1093/oxfordjournals.jbchem.a133902.

Abstract

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.

MeSH terms

  • Amino Acids / chemical synthesis*
  • Ammonia*
  • Chemical Phenomena
  • Chemistry
  • Glyoxylates

Substances

  • Amino Acids
  • Glyoxylates
  • Ammonia
  • glyoxylic acid