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Synthesis and Properties of ApA Analogues with Shortened Phosphonate Internucleotide Linkage.
- Source :
- Nucleosides, Nucleotides & Nucleic Acids; Jul/Aug2011, Vol. 30 Issue 7/8, p524-543, 20p
- Publication Year :
- 2011
-
Abstract
- A complete series of the 2 '-5 ' and 3 '-5 ' regioisomeric types of r(ApA) and 2 '-d(ApA) analogues with the α-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 α-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 α-hydroxy-phosphonate linkage in modified oligoribonucleotides is discussed. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 15257770
- Volume :
- 30
- Issue :
- 7/8
- Database :
- Complementary Index
- Journal :
- Nucleosides, Nucleotides & Nucleic Acids
- Publication Type :
- Academic Journal
- Accession number :
- 65184717
- Full Text :
- https://doi.org/10.1080/15257770.2011.581259