The evolution of nucleotides

Examples of chiral selection in nonenzymatic aminoacylation of internal 2-prime hydroxyl groups of oligo- and polynucleotides are discussed as an evidence for the early evolution of bionucleotides. Some factors that could influence the degree of this chiral selection and its direction are discussed. These include the structure of the aminoacyl component, the structure of the nucleoside component, and the reaction conditions. Investigation of the mechanism of this reaction was aided by the use of 3-prime inosine methyl phosphate (as a simplified model for a dinucleoside monophosphate) and proton NMR spectroscopy of t-butoxycarbonyl-alanyl esters of nucleosides as models for the transition state of the aminoacylation reaction itself.