Studies on a potentially prebiotic synthesis of RNA

Article abstract of DOI:10.1016/S0040-4020(97)00466-3

Current thinking supports an early phase of evolution in which information transfer and catalysis were mediated by evolving RNA. A novel potentially prebiotic synthesis of RNA is proposed involving polymerisation through aldol condensation followed by a retro-Amadori rearrangement and ring closure via a base-paired mesomeric heterocyclic betaine intermediate. The proposed monomer 1 is an achiral mixed phosphodiester and herein we report synthetic routes to 1 containing each of the four RNA bases, The solution phase behaviour of 1 containing adenine and uracil has been investigated and preliminary results of polymerisation experiments are also presented.