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2'-Fluoro-2'-deoxynucleoside-3'-CE-phosphoramidites The 2'-F-RNA oligonucleotide adopts an A-form helix on hybridization to a target. Whereas a hydroxyl group of RNA is a hydrogen bond donor, fluorine of 2'-F-RNA appears to be a weak acceptor. These features of 2'-F-RNA oligonucleotides lead to certain interesting properties. For example, it was demonstrated that oligonucleotides hybridize to a RNA oligonucleotide in the following order of increasing stability: DNA < RNA < 2'-OMe-RNA < 2'-F-RNA.1 The Aptamers, composed of 2'-F-RNA bind targets with higher affinities and are more resistant to nucleases, compared to RNA aptamers.2 In addition to that, 2'-F-RNA can be effectively used in siRNA applications. It was clearly demonstrated that siRNA synthesized with 2'-F pyrimidine nucleosides3 and also with 2'-F purine nucleosides4 were more inhibitory and showed considerably increased stability in human plasma compared to siRNA. They were absolutely functional in both, cell culture and in vivo. Metkinen Chemistry is making available building all 4 building blocks for the synthesis of 2'-F-RNA oligonucleotides. These blocks are: 2'-Fluoro-2'-deoxyguanosine-3'-CE-phosphoramidite, 2'-Fluoro-2'-deoxyadenosine-3'-CE-phosphoramidite, 2'-Fluoro-2'-deoxycytidine-3'-CE-phosphoramidite, 2'-Fluoro-2'-deoxyuridine-3'-CE-phosphoramidite. They are offered either separately or as a set of 4. REFERENCES: 1. A.M. Kawasaki, et al., J. Med. Chem., 1993, 36, 831-841. 2. M. Khati, M. Schuman, J. Ibrahim, Q. Sattentau, S. Gordon, and W. James, J. Virol., 2003, 77, 12692-12698. 3. J.M. Layzer, A.P. McCaffrey, A.K. Tanner, Z. Huang, M.A. Kay, and B.A. Sullenger, RNA, 2004, 10, 766-771. 4. Muchonen, P., Tennilä, T., Azhayeva, E., Parthasarathy, R., N., Janckila, A., Väänänen, K., Azhayev, A., Laitala-Leinone, T Chemistry & Biodiversity 2007, in press. |
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