Current thinking supports an early phase of evolution in which informa
tion transfer and catalysis were mediated by evolving RNA. A novel pot
entially prebiotic synthesis of RNA is proposed involving polymerisati
on through aldol condensation followed by a retro-Amadori rearrangemen
t and ring closure via a base-paired mesomeric heterocyclic betaine in
termediate. 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 u
racil has been investigated and preliminary results of polymerisation
experiments are also presented. (C) 1997 Elsevier Science Ltd.