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

Beier, M; Reck, F; Wagner, T; Krishnamurthy, R; Eschenmoser, A · Science · 1999

other · Level V

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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.

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