Issue 17, 2011
From the journal:

Organic & Biomolecular Chemistry

Synthesis of oligoribonucleotides with phosphonate-modified linkages†

Ondřej Páv,a   Ivana Košiová,a   Ivan Barvík,b   Radek Pohl,a   Miloš Buděšínskýa  and  Ivan Rosenberg*a  

* Corresponding authors

a Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nam. 2, Prague, Czech Republic
E-mail: ivan@uochb.cas.cz
Fax: +420 220 183 531
Tel: +420 220 183 381

b Institute of Physics, Faculty of Mathematics and Physics, Charles University, Ke Karlovu 5, Prague 2, Czech Republic
E-mail: ibarvik@karlov.mff.cuni.cz
Fax: +420 224 922 797
Tel: +420 221 911 450

Abstract

Solid phase synthesis of phosphonate-modified oligoribonucleotides using 2′-O-benzoyloxymethoxymethyl protected monomers is presented in both 3′→5′ and 5′→3′ directions. Hybridisation properties and enzymatic stability of oligoribonucleotides modified by regioisomeric 3′- and 5′-phosphonate linkages are evaluated. The introduction of the 5′-phosphonate units resulted in moderate destabilisation of the RNA/RNA duplexes (ΔTm −1.8 °C/mod.), whereas the introduction of the 3′-phosphonate units resulted in considerable destabilisation of the duplexes (ΔTm −5.7 °C/mod.). Molecular dynamics simulations have been used to explain this behaviour. Both types of phosphonate linkages exhibited remarkable resistance in the presence of ribonuclease A, phosphodiesterase I and phosphodiesterase II.

Graphical abstract: Synthesis of oligoribonucleotides with phosphonate-modified linkages

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Article information

DOI
https://doi.org/10.1039/C1OB05488K
Article type
Paper
Submitted
29 Mar 2011
Accepted
14 Jun 2011
First published
15 Jun 2011

Org. Biomol. Chem., 2011,9, 6120-6126

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Synthesis of oligoribonucleotides with phosphonate-modified linkages

O. Páv, I. Košiová, I. Barvík, R. Pohl, M. Buděšínský and I. Rosenberg, Org. Biomol. Chem., 2011, 9, 6120 DOI: 10.1039/C1OB05488K

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