253875-07-9Relevant academic research and scientific papers
Pentopyranosyl oligonucleotide systems. Part 11: Systems with shortened backbones: (D)-β-ribopyranosyl-(4′→3′)- and (L)-α-lyxopyranosyl-(4′→3′)-oligonucleotides
Wippo, Harald,Reck, Folkert,Kudick, Rene,Ramaseshan, Mahesh,Ceulemans, Griet,Bolli, Martin,Krishnamurthy, Ramanarayanan,Eschenmoser, Albert
, p. 2411 - 2428 (2007/10/03)
Th (L)-α-lyxopyranosyl-(4'→3')-oligonucleotide system - a member of a pentopyranosyl oligonucleotide family containing a shortened backbone - is capable of cooperative bas -pairing and of cross-pairing with DNA and RNA. In contrast, corresponding (D)-β-ribopyransoyl-(4'→3' )-oligonucleotides do not show base-pairing under similar conditions. We conclude that oligonucleotide systems can violate the 'six-bonds-per-backbone-unit' rule by having five bonds instead, if their vicinally bound phosphodiester bridges can assume an antiperiplanar conformation. An additional structural feature that seems relevant to the cross-pairing capability of the (L)-α-lyxopyranosyl-(4'→3')-oligonucleotide system is its (small) backbone/ basepair axes inclination. An inclination which is similar to that in B-DNA seems to b a prerequisite for an oligonucleotide system's capability to cross-pair with DNA. Copyright
