The formation of peptides from the 2'(3')-glycyl ester of a nucleotide.
We have synthesized 2'(3')-O-(glycyl)-adenosine-5'-(O-methylphosphate), 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.
D000249:Adenosine Monophosphate / Q000031:analogs & derivatives*; D005075:Biological Evolution; D004952:Esters; D005998:Glycine / Q000031:analogs & derivatives; D006863:Hydrogen-Ion Concentration; D000069497:Origin of Life; D010455:Peptides / Q000138:chemical synthesis*
D004952:Esters; D010455:Peptides; D000249:Adenosine Monophosphate; D005998:Glycine