Oligo Synthesis : CEPs

Catalog Number: 10-3800-xx

Description: 2"-FANA-A-CE Phosphoramidite

2’-F-Arabinonucleic Acid (2’-F-ANA)

Arabinonucleosides are epimers of ribonucleosides with the chiral switch being at the 2’ position of the sugar residue. 2’-F-ANA adopts a more DNA-like B-type helix conformation, not through the typical C2’-endo conformation but, rather, through an unusual O4’-endo (east) pucker. However, the presence of the electronegative fluorine leads to a still significant increase (DTm1.2° C/mod) in melting temperature per modification.1 2’-F-ANA-containing oligonucleotides exhibit very high binding specificity to their targets. Indeed, a single mismatch in a 2’-F-ANA – RNA duplex leads to a DTm of -7.2 °C and in a 2’-F-ANA - DNA duplex a DTm of -3.9 °C.2

The presence of fluorine at the 2’ position in 2’-F-ANA leads to increased stability to hydrolysis under basic conditions relative to RNA and even 2’-F-RNA.1,3 The stability of 2’-F-ANA to nucleases also makes this a useful modification for enhancing the stability of oligonucleotides in biological environments.2 2’-F-ANA hybridizes strongly to target RNA and, unlike most 2’ modifications, induces cleavage of the target by RNase H. Phosphorothioate (PS) 2’-F-ANA is routinely used in these applications due to its increased nuclease resistance. Alternating 2’-F-ANA and DNA units provide among the highest potency RNase H-activating oligomers. Both the “altimer” and “gapmer” strand architectures consistently outperform PS-DNA and DNA/RNA gapmers.4

siRNA oligos were found to tolerate the presence of 2’-F-ANA linkages very well. High potency gene silencing was demonstrated5 with siRNA chimeras containing 2’-F-RNA and/or LNA and 2’-F-ANA. The high efficacy of these chimeras was attributed to the combination of the rigid RNA-like properties of 2’-F-RNA and LNA with the DNA-like properties of 2’-F-ANA.

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MSDS

Glen Report 22.2

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1. E Viazovkina, M M Mangos, M I Elzagheid, and M H Damha, Curr Protoc Nucleic Acid Chem., 2002, chapter 4, Unit 4 15
2. J K Watts, and M J Damha, Can J Chem., 2008, 86, 641-656
3. J K Watts, A Katolik, J Viladoms, and M J Damha, Org Biomol Chem., 2009, 7, 1904-10
4. A Kalota, et al., Nucleic Acids Res., 2006, 34, 451
5. G F Deleavey, et al., Nucleic Acids Res., 2010, 38, 4547-4557
6. J K Watts, et al., Nucleic Acids Res., 2007, 35, 1441-1451
7. T Dowler, et al., Nucleic Acids Res., 2006, 34, 1669-1675

2"-F-ANA is covered by intellectual property. Key patents covering siRNA and antisense applications are as follows:

WO/2009/146556 (siRNA)

WO 03064441 and WO 0220773 (antisense)

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2"-F-ANA is covered by intellectual property. Key patents covering siRNA and antisense applications are as follows:

WO/2009/146556 (siRNA)

WO 03064441 and WO 0220773 (antisense)

If you cannot find the answer to your problem below then please contact us or telephone 01954 210 200

DILUTION/COUPLING DATA

The table below shows pack size data and, for solutions, dilutions and approximate couplings based on normal priming procedures.

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