Chemical etiology of nucleic acid structure: comparing pentopyranosyl-(2'-->4') oligonucleotides with RNA

Abstract

All four members of the family of pentopyranosyl-(2'-->4') oligonucleotide systems that contain beta-ribo-, beta-xylo-, alpha-lyxo-, or alpha-arabinopyranosyl units as repeating sugar building blocks are found to be much stronger Watson-Crick base-pairing systems than RNA. The alpha-arabinopyranosyl system is the strongest of all and in fact belongs to the strongest oligonucleotide base-pairing systems known. Whatever the chemical determinants by which nature selected RNA as a genetic system, maximization of base-pairing strengths within the domain of pentose-derived oligonucleotide systems was not the critical selection criterion.