The formation of dipeptides from amino acids and the 2′(3′)-glycyl ester of an adenylate
- 1 September 1979
- journal article
- Published by Springer Nature in Journal of Molecular Evolution
- Vol. 13 (3), 185-191
- https://doi.org/10.1007/bf01739478
Abstract
The yields of dipeptide obtained from the reaction of 0.2M 2'(3')-O-(glycyl)-adenosine-5'-(O-methylphosphate) and 0.2M amino acid at pH 8.2 ranged from 0.1% to 35.5% for a group of 15 amino acids. The yields of glyser (35.3%), gly-cys (11.8%) and gly-thr (5.4%) were considerably greater than dipeptide yields obtained from any of the other 12 amino acids (less than or equal to 1.7%). Aminolysis of 0.05M 2'(3')-O-(glycyl)-adenosine-5-'-(O-methylphosphate) by 0.4M serine ethyl ester yielded 53% glycylserine diketopiperazine, via N-(glycyl)-serine ethyl ester as a transient intermediate. The prebiotic significance of these reactions is discussed.Keywords
This publication has 14 references indexed in Scilit:
- The formation of peptides from the 2′(3′)-glycyl ester of a nucleotideJournal of Molecular Evolution, 1978
- Amino acid activation with adenosine 5′-phosphorimidazolideJournal of Molecular Evolution, 1978
- N, N′-carbonyldiimidazole-induced diketopiperazine formation in aqueous solution in the presence of adenosine-5′-monophosphateJournal of Molecular Evolution, 1976
- On the chemical reactivity of aminoacyl-tRNA ester bond: I - Influence of pH and nature of the acyl group on the rate of hydrolysisBiochimie, 1974
- On the chemical reactivity of aminoacyl-tRNA ester bond: II. Aminolysis by tris and diethanolamineBiochimie, 1974
- Reaction of tris-(hydroxymethyl)-aminomethane with valyl-TYMV-RNABiochimie, 1971
- The general synthetic route to amino acid esters of nucleotides and nucleoside-5′-triphosphates and some properties of these compoundsTetrahedron, 1970
- Kinetics of the Reactions of O-Acetylethanolamine.Acta Chemica Scandinavica, 1963
- Intramolecular S-O and S-N Acetyl Transfer ReactionsJournal of the American Chemical Society, 1962
- Rearrangements between Primary Ethanolamides of Carboxylic Acids and the Corresponding Aminoethylesters*Journal of the American Chemical Society, 1947