Amino acid synthesis from formaldehyde and hydroxylamine

The experiments reported here have shown that by heating an aqueous mixture of formaldehyde and hydroxylamine hydrochloride, several amino acids, hydroxy acids, and other biochemical compounds are formed, the predominant amino acid formed is glycine.

Abstract

The experiments reported here have shown that by heating an aqueous mixture of formaldehyde and hydroxylamine hydrochloride, several amino acids, hydroxy acids, and other biochemical compounds are formed. The predominant amino acid formed is glycine. The conditions under which the reaction takes place have been studied in some detail. The mechanism of synthesis has also been studied. Formaldoxime, hydrogen cyanide, and ammonia are among the first products formed. Strecker and cyanohydrin condensations yield nitriles which are subsequently hydrolyzed to amides and finally to acids. Other condensation reactions are proposed to account for the formation of serine, alanine, β-alanine, and lactic acid. The interpretation of some previous photochemical syntheses of amino acids appears possible in the light of the present evidence. The experiments are of significance in relation to the formation of biochemical compounds, from simple compounds of carbon and nitrogen, under conditions assumed to have existed during the early development of the earth's crust.