The formation of peptides from the 2′(3′)-glycyl ester of a nucleotide

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Abstract
We have synthesized 2′(3′)-O-(glycyl)-adenosine-5′-(O-methylphos-phate), an analogue of the 3′-terminus of aminoacylated tRNA. A 0.4M solution of this compound maintained at pH 8.2, yields 5.5% of diglycine and 11.5% of diketopiperazine, in addition to the hydrolysis products glycine and adenosine-5′-(O-methylphosphate). Under the same conditions, glycine ethyl ester reacts much more slowly, but ultimately gives similar yields of diglycine and diketopiperazine. The aminolysis of 2′(3′)-O-(glycyl)-adenosine-5′-(O-methylphosphate) by free glycine is relatively inefficient, but serine reacts 20 times more rapidly and yields up to 50% of N-glycylserine. The prebiotic significance of these reactions is discussed.