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Relevant academic research and scientific papers

Synthesis and properties of ApA analogues with shortened phosphonate internucleotide linkage

A complete series of the 2'-5' and 3'-5' regioisomeric types of r(ApA) and 2'-d(ApA) analogues with the-hydroxy-phosphonate C3'-O-P-CH(OH)-C4" internucleotide linkage, isopolar but non-isosteric with the phosphodiester one, were synthesized and their hybridization properties with polyU studied. Due to the chirality on the 5'-carbon atom of the modified internucleotide linkage bearing phosphorus and hydroxy moieties, each regioisomeric type of ApA dimer is split into epimeric pairs. To examine the role of the 5'-hydroxyl of the-hydroxy-phosphonate moiety during hybridization, the appropriate r(ApA) analogues with 3'(2')-O-P-CH2-C4" linkage lacking the 5'-hydroxyl were synthesized. Nuclear magnetic resonance (NMR) spectroscopy study on the conformation of the modified sugar-phosphate backbone, along with the hybridization measurements, revealed remarkable differences in the stability of complexes with polyU, depending on the 5'-carbon atom configuration. Potential usefulness of the-hydroxy-phosphonate linkage in modified oligoribonucleotides is discussed. Copyright Taylor and Francis Group, LLC.